This has been something on my mind that I just can't seem to shake off.

Backstory: My family has a group of other families that we regularly meet up with. We vacation, have dinners, etc. My dad has a pretty close friend among the group. Let's call him Vic. Vic has a wife (who he's pretty distant and unaffectionate towards) and a family. He is undeniably handsome and has a mysterious aura. Vic is always charismatic and lively, which is very refreshing considering that my culture (South Asian) is full of more conservative people.

Dilemma: When I turned about 17 or 18 I noticed Vic started looking at me differently, I caught him almost staring at me several times. He tends to stare at my chest area if I happened to wear anything particularly low cut, slightly smiles (almost smirks) and gives me a glance from top to bottom. Besides the physical heat, he treats me with a sense of maturity compared to the other girls that are my age in the group. I felt that he sometimes went out of his way to make slight physical contact as well as eye contact. Like I said, Vic is beyond handsome. There is no denying that I am attracted to him and his personality. I find myself daydreaming about him and desperately wanting to see him more often. The age gap is not the issue for me, as I am typically attracted to older men. The only problem is the obvious. He has a family and I am essentially his friend's daughter.

My only question is: How do I approach a conversation about this with him (if there is any to be had). I don't want to be some sort of home wrecker, but he is giving me signals as if he wants something. I am so confused.

For reference: Both of us are from South Asia, but living in America. I am currently 21 and he is 44.

Update: I know subconsciously, that I want for something to be there between us. I just don't know how to go about approaching a situation where I can make that happen, if that makes sense.

Update 2: Thank you everyone for your insightful answers! Just for some clarification, I do NOT expect to have any sort of long term relationship with Vic. I live my life through practicality, and know that that is not something that would be plausible, or even a good idea. Some people have understood my dilemma spot on: I am physically attracted to this man. I have been so inside my head lately about what to do about it. I just want to know if talking to him/responding or reciprocating his flirtations are a good idea. Yes I am 21 years old, and at this age I "don't have the mental capabilities etc etc." I want to remind you all that I am by no means a careless middle school/high school student. I'd love any more answers/feedback you all may have!

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    I think this is a very difficult question for IPS to answer. Generally speaking, in most cultures that I am aware of, this kind of relationship is frowned upon. This means the OP is specifically asking for advice on the kind of relationship which challenges typical rules about how relationships "should" work. This means there's only two possible answers. We can say "don't," or we can look at you and him as an individual, and try to understand why this relationship wouldn't fit the normal rules. We won't have that kind of information in 2 paragraphs. – Cort Ammon Oct 18 '17 at 23:26
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    'Yes I am 21 years old, and at this age I "don't have the mental capabilities etc etc."' Seriously? You're 21. You're an adult. You really can't use the "I'm too young to know what's going on" excuse any more. – David Richerby Oct 22 '17 at 12:56
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    Your story sounds odd to me. You are longing for a man who's both handsome and has a nice personality, while at the same time you suspect him of leaving his family for some young plaything? Very nice person indeed... – Geliormth Dec 20 '17 at 0:26

13 Answers 13

The default reaction of people these days is "I'm not gonna judge", but ...

I'm going to go there.

But first I'll address your actual question, then you can stop reading. ;D The problem is that you don't have any way of telling if he is actually into you, if he's just enjoying the occasional peek at a vibrant young lady, or if you're misreading the cues. Note carefully that he hasn't approached you. So whatever his feelings are, they aren't overwhelming him.

Okay, now the judgy part...

Honestly this doesn't seem like a good idea. You don't know this guy has an actual emotional desire for you, or just a minor "middle-aged lech" eye-candy thing for you.

If you approach him and you're wrong, there's a whole new world of mortification waiting for you.

If you approach him and you're right, the consequences for all parties involved -- your father, the guy, his wife, his children -- could be disastrous. There are many reasons, religious, moral, and well, practical that there's a generally-understood "no poaching" rule.

If you really want internet strangers' advice, I'll recommend as strongly as possible that you let this one go.

  • Comments are not for extended discussion; this conversation has been moved to chat. – Catija Oct 19 '17 at 23:15
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    "If you approach him and you're wrong, there's a whole new world of mortification waiting for you" Source please. – Andreas Oct 20 '17 at 19:18
  • @Andreas: Ha. I see what you did there. – Robert Harvey Oct 20 '17 at 19:52
  • @Andreas eventually someone will come along and move comments to chat, saving me from having to cough up the scurvy details... ;D – akaioi Oct 22 '17 at 20:03
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    I agree with this answer, but I must stress this: «Note carefully that he hasn't approached you. So whatever his feelings are, they aren't overwhelming him.» - it should be noted that she hasn't approached him either, and yet her feelings are overwhelming her; this disproves the logic in your answer, akaioi. – ANeves Feb 6 at 16:29

My only question is: How do I approach a conversation about this with him (if there is any to be had). I don't want to be some sort of home wrecker, but he is giving me signals as if he wants something. I am so confused.

I'm not sure what you're confused about. Are you confused because he's giving indications of being attracted to you though he has a wife? Both can coexist. People cheat. (If that's not what you're confused about, please edit to specify, and I'll edit my answer accordingly.) People also flirt, sometimes just for fun and sometimes to find out who will cheat with them.

If you don't want to be some sort of homewrecker, don't engage in anything questionable (including flirting, responding to his flirting, and having conversations about your feelings towards him or his towards you) until after he's divorced. That way, you also allow your dad to keep his friend for a while longer.

Once he's divorced (without any encouragement from you, since you don't want to be a homewrecker), he's on the market, and you can have that conversation. Be aware, though, that your dad is likely to be very unreceptive to his friend and you being an item. But if he really makes you happy, your dad may come around in time.

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    The 23 year age gap may be worth addressing here. Not trying to judge, some people make it work, but it's probably worth addressing. Otherwise this seems like a reasonable answer. – apaul Oct 18 '17 at 0:52
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    But this guy may or may not get divorced anytime soon. – Revetahw Oct 19 '17 at 4:54
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    @Revetahw Doesn't matter, if you don't want to be a homewrecker, he's off the market for as long as he's married, whether he gets a divorce ever or not. The only way to not be a homewrecker are two negative options, and one is more plausible than the other; the way in which anon addressed. – Anoplexian Oct 19 '17 at 15:59
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    I suppose @Revetahw meant that the situation can go on indefinitely without a resolution @ Anoplexian. The reply is implicit in @ anongoodnurse's answer: if he does not get a divorce then he does not care to be serious about OP: that is itself his reply to OP. – English Student Oct 20 '17 at 5:18
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    People cheat, some flirt, but also some just look. It's entirely possible that Vic is 100% devoted to his wife and has zero intention of cheating on her, but also enjoys looking at attractive young 20-somethings, perfectly happy to never even take it so far as flirting (which some would consider cheating.) – corsiKa Oct 20 '17 at 17:21

Short version : Both your behaviors are inappropriate, but the age difference and connection makes that doubly bad for him.

There's a rule of thumb : you should not be dating or in a relationship with someone whose age is less than around half you age plus seven years.

"Vic" is 44. That rule of thumb puts his lower limit age range at about 29.

So you're way out of the "recommended sane range" for Vic.

But what's far worse is that he started eying you up when you were 17. That's under legal age in many places and you were a friend's daughter - that's off limits by any normal expected behavior for a guy.

And he's married. Is there any rule of behavior this guy doesn't break ?

So his behavior is that of a very selfish and creepy guy. Now I'm going by your description, and that may not be entirely accurate, but it's what I have to go on.

Do not trust him.

And a rule for you : marriages look different from the outside than the inside. Don't ever get involved with someone married. Ever. Get involved with a married person when they're divorced (not separated, because they go back to the wives a lot of the time).

How do I approach a conversation about this with him (if there is any to be had). I don't want to be some sort of home wrecker, but he is giving me signals as if he wants something.

He wants something. And he'll possibly use you for sex and then dump you when the going gets tough. He'll say what you want to hear (if he's what I think) and then when you look for more than he wants to give, you'll be dumped.

I've seen this before and it's hurt friends of mine. A lot and for a long time.

I am so confused.

You're young (even at 21), that's natural.

And a guy like this can ruin your young life.

Put it to you this way : how would you feel if your Dad were behaving like this guy to one of your friends ? Would you encourage her to have a relationship with your Dad ? I'm guessing we both know the answer to that.

For reference: Both of us are from South Asia, but living in America. I am currently 21 and he is 44.

Honestly if he was a younger (say 30) and actually single I'd say good luck to you both and take your chances.

He's not.

Update: I know subconsciously, that I want for something to be there between us. I just don't know how to go about approaching a situation where I can make that happen, if that makes sense.

What you want is sometimes something you should walk away from.

This rule works for desserts, jobs and, sad to say, relationships.

And here's a scary thought for ya : this sort of feeling probably won't ever go away. I'm older than you (and Vic) and I still get that kind of "run headlong into fire" sensation. It's just that experience has taught me two things :

  • Fire burns and touching it leaves scars
  • The fire will pass and then one day you'll find a source of warmth that doesn't burn and lasts longer (and isn't 23 years older :-)).

There'll be plenty of better chances for romance, but this is the one where you learn to walk away from your desire. Learning to know when to follow your desires and when to trust them is a lot of this stage of your life.

But not Vic. My gut says Vic is a creep. :-)

And P.S. As an older guy I'm 100% for women liking older men. But there are sane limits and this isn't one of them.

This time you should suffer your desire in silence and it will pass.

And in a properly written script Mr. Right will turn up after that. :-)

Response to OP's Update 2

What you are in essence saying is that you have a desire for a physical, but not deeply romantic, relationship with this older married man.

First of all note that you've previously said you did find him charismatic or romantic. So you have all the signs of someone trying to say the equivalent of "I can stop any time I want to, so it can't hurt to start"

It's as simple as this : he's married and ( being as broadminded as possible here ) it would be morally wrong without the wife's full consent. Wives normally don't go for that idea.

What about your desire if she's not willing ? Tough luck.

Life doesn't provide you with everything you want, no matter how badly. Sometimes you have to walk away and this is more than likely one of them.

The question of should you do it behind the wife's back is a simple moral one. No one but you and the husband can make that decision. But it would be morally wrong period.

Should you do it if the wife does consent ?

I would strongly advise against it.

Sex combined with your apparent romantic interest is an overpowering cocktail for anyone (regardless of age). Even if you entered this expecting nothing more than a sexual relationship, you will often find that that will not last long and you'll want more. And that's especially the case if it all works out well without other problems.

In your original post you indicated you considered the man and his wife's relationship to be difficult, perhaps in trouble.

First of all this is a very hard call to make from outside a relationship. You'd be amazed how robust some relationships can be between people who, on the surface, bicker and squabble. It's not that simple inside a long term relationship. So be wary of surface impressions.

Secondly, if their relationship is in trouble you should not stick yourself in the middle of something that might be merely a difficult period for them (I think all long term relationships have these). This is where the term home-wrecker comes in. Please don't be one.

Lastly I'll cover an option you may be considering : trying to have a platonic but deep relationship with the man.

Again, I think this would be a bad choice. It's like picking up a drink in a bar and saying you don't want it, but not putting it down. Eventually you'll do something (or more precisely both of you will) which is one of the poor choices I mentioned.

I'm not saying you can't be friends. I'm saying it's a bad idea to pursue such a friendship when your head, heart and hormones are looking for more.

So my strong advice to you is to walk away from your desire. It's a good lesson to learn for your life : be in control of your desires, not the other way around.

That doesn't make you less passionate. But it would make you stronger and less open to damaging life choices.

Remember finally that when you get involved with a married man, you're really involving yourself in his wife's relationship as well. And perhaps his children's, if he has any.

So there's more than you involved in these choices.

I want to remind you all that I am by no means a careless middle school/high school student.

With respect, what you are having trouble with is controlling your desires. With more maturity you will gain that. And if you were as mature a thinker as you may feel you are, you would not need advice.

But Vic's flirtations (taking your view of them on face value) indicate someone with dubious moral priorities. I addressed this in my first response and I'd remind you to consider those views again. Pursuing a relationship with a free agent is one thing : Vic is not a free agent.

  • Comments are not for extended discussion; this conversation has been moved to chat. – Catija Oct 31 '17 at 5:13

In both question and answer I see a fundamental myth perpetuated that is spread through a host of romantic books and motion pictures: that a mutual attraction is something unique that warrants acting upon.

It isn't. In the supermarket and in restaurants food is presented in appetizing manners and we are not expected to bite into the exhibits and/or buy all that appeals to us.

In a similar vein, sexual attraction is a rather basic feeling that only has the meaning we ascribe to it.

Acting upon it without considering the consequences reduces man to animal. You look at the price tag, check whether it's worth the expense, and if not, move on.

You don't have the necessary experience for comparing the price tags. Vic should have. He is not after your intellect since you have not yet had a whole lot of time and experience to develop it. However, there is quite less for him at risk than for you: even if our information is filtered through your rose-tinted glasses, he does not seem to care a whole lot for his wife, so basically it's his friendship with your father that could be jeopardized. That, however, is a lot more replaceable than your ties with your family.

Apart from your fawning over his "mysterious" aura (which is straight out of Jane Austen novels and Twilight movies), your main attraction to him seems to be his apparent interest in your features. Which Western clothing is designed to accentuate, so for better or worse, his perceiving you as female and attractive is not as such unusual but rather "working" as intended.

Acting on such a perception is a completely different thing. There are cultures where this is not understood well and females have to cover themselves completely up in clothes not allowing them to be perceived as such.

That's overall a worse option in my book. But in your case, you ascribe more meaning to the effects of our more interesting approach than is good for you.

You don't have the kind of life experience to feel certain about such decisions, but I would strongly suggest that you forget about Jane Austen and Twilight approaches to your current situation and try gradually defusing it mainly for your own sake. This may sound sort of stupid, but you might want to dress more conservatively when you know he's around and thus avoid feeding your mutual attention.

And if you want to entertain notions of being destined for each other and everlasting love, there's no harm in waiting out five years or so before acting. If his personal situation hasn't changed by then, it can't be that inconvenient for him. And more likely than not, you'll have a different outlook on life and love by then.

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    I agree with this answer wholeheartedly, but I find the allusion to Jane Austen to be highly incongruous and peculiar. All three of Austen's books that I've personally read display with some detail the highly negative consequences of treating mutual attraction as of higher importance than morals or ethics. Twilight is a much more appropriate comparison. – Wildcard Oct 18 '17 at 23:47
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    This. I don't know Vic, but from the description it doesn't sound as if he's interested in more that just looking at her. And if he's been married to the same wife for half his life, maybe it will look to the outside world like he's not really that interested in her any more, while in reality he may have no intention of ever divorcing or cheating. – Mr Lister Oct 20 '17 at 7:19
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    "there is quite less for him at risk than for you" - How could you possibly suggest that? He's a grown man with a life and a family. If the OP is naive enough to believe a relationship with her father's friend, 20+ years her senior, might actually work then do you really trust her assessment of the health of this guy's marriage? – user2904 Oct 20 '17 at 13:41
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    @DanK I agree. Risk for her: both families displeased and dislike her. Risk for him: losing home, dirty divorce, loss of money/items, family might turn their back on him, even possibility of losing job. PLUS both families displeased and dislike him – user3316 Oct 20 '17 at 17:27

I'm going to break your question down into parts:

How do I approach a conversation about this with him (if there is any to be had).

Don't have a conversation with him.

I don't want to be some sort of home wrecker,

Then don't.

but he is giving me signals as if he wants something.

Indeed he is. You should avoid him.

I am so confused.

You're not actually confused, what's happening is you have conflicting desires.

Desire 1: you want to be a good person (you don't want to contribute to his wife and his kids feeling the pain of betrayal).

Desire 2: Apparently you're attracted to him and want a sexual relationship with him.

You can't full fill both desires. You will have to sacrifice one in order to get the other.

We have to do this all the time in life. Sacrifice one of our desires or goals for a more important desire or goal

So choose which Desire is more important to you and follow it. Knowing full well you have rejected the other.

Which Desire should you choose?

My advice, stay away from this man.

Why?

  1. Encouraging him in any way will most likely lead to his betraying his family. Which means you will have contributed to his wife and children's suffering. (This includes talking to him and smiling at him, he will see these actions as encouragment.)

  2. It seems likely from your question that a relationship with this man would cause disruption in your own family as well. So that's extra pain and suffering in your life that you could avoid.

  3. If he will betray his Wife who he is expressly committed to then he'll most likely betray you too.

Solution: Go find some one who is unattached to start a relationship with.

Go dancing, join some clubs, or start dating online. Go out in the world and meet other men. You can find someone else who you are attracted to, to start a relationship with. There are a lot of upstanding, attractive, single men out there for you. If you go look for them you'll find them. And you can be a good person while doing it.

I am assuming you are a 21 year-old woman and this is a real-life situation rather than a creatively 'representative' question for all young women attracted to older men.

So all these wonderful answers have given you a full and in-depth overview of all possible outcomes to this situation. Most of these kind members have advised you to take no action at present, but I would beg to differ and tell you to do what you really want to do.

Because you are a woman and in these modern times there are no real social restrictions on what is appropriate for a woman to do in such situations, especially in your country of residence (if not your country of origin.) Others may disapprove of your decisions but you can make your own choices, just like any man.

You can be who you want, you can do what you want: you can jump on any man you want. Just be prepared to take full responsibility for the consequences.

As I would urge all members to recollect, your 'only question' was

how do I approach a conversation about this with him (if there is any to be had). I don't want to be some sort of home-wrecker etc etc etc

Well, the direct approach through verbal or non-verbal communication probably works best in such situations, though Ivan Skalauh's answer has also suggested an 'indirect approach' which is 'safer' for this man and also reduces your risk of rejection -- but beware: home-wrecking might be a likely outcome of any such action.


Note: accepting an answer by clicking the nearby tick mark (turns grey-to-green) is OP's powerful 'casting vote' when different answers give contrasting advice. If any answer here suits your requirements best, please accept it to signal your choice to the Interpersonal Skills community.

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    EnglishStudent, interesting approach; I don't want to derail discussion of OPs issue, but as one of those awful finger-wagging moralizers may I raise an eyebrow at the notion that "I really really want to!" is all the justification one needs to hurt several lives? I know we're in a pendulum swing away from a highly-moralistic era and all, but ... um. OP is not the only one who will be taking those consequences, yo. – akaioi Oct 20 '17 at 5:16
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    I thought long and hard about it and came to the conclusion that after reading all our good advice covering all consequences, OP will do exactly what she wants to do @akaioi -- that's why I want her to be prepared to take responsibility for all the consequences of her decision. In short I am saying: if a family breaks up as a result of your actions then be aware you shall be responsible for that result. I asked a question about a similar situation last month: interpersonal.stackexchange.com/questions/4269/… – English Student Oct 20 '17 at 5:21
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    @EnglishStudent "OP will do what she wants to do" yep, true words. I think a lot of this thread is people trying to get OP to reconsider what she wants... Well, another old quote... "Life is the best teacher" – akaioi Oct 20 '17 at 5:30
  • "Ultimately, it's her decision, and telling her what to do will likely backfire." __ This answer (which I accepted) to that question is equally relevant to OP here @ akaioi: interpersonal.stackexchange.com/a/4285/381 -- luckily my cousin reconsidered, decided she wants more time, and postponed marrying that Joe person by 6 months. Time and experience teach a person to better understand about others' motivations. So give it time! That's what @anongoodnurse wanted OP to do by saying in her answer: if you don't want to be a home-wrecker then don't approach him until he gets a divorce. – English Student Oct 20 '17 at 5:37
  • I found I have earlier made the 'taking responsibility for the consequences' point in a similar situation in my this comment under that accepted answer to my last month's question @akaioi: interpersonal.stackexchange.com/questions/4269/… – English Student Oct 20 '17 at 5:49

anongoodnurse's answer covered most of the question pretty well, but I think there's a pretty important caveat to be considered with such a large age gap...

Assuming for the sake of argument that he does get divorced and you're free to pursue something more with him. Have you really thought that through?

  • I'm guessing that since you said that he has a family and that he's 44, that his children are closer to your age. Are you prepared to be a step mother to someone who may be your age or only a few years younger?

  • Have you considered that by the time you're in your 40's he'll be in his mid-sixties?

  • If you were to get married and have children, people would likely assume that they're his grandchildren and that you're his daughter.

  • Have you thought about the vast differences in life experience between 21 and 44? He probably remembers the cold war, new wave music, and a lot of other things that you kinda had to be there for to fully understand.

  • Likewise you probably have interests and hobbies that a man in his 40's doesn't really understand or relate to.

I'm not saying that any of these things are deal breakers, or that they should be. They're just things worth thinking about before pursuing anything.

Also keep in mind that some men have an eye for younger women, and it's often not for the best reasons. The attention that he's showing you, and not to his wife, may be something that he carries into the relationship that he might have with you... More or less, it may be wonderful for the first few years, but he may be looking to trade you in for a younger model when you begin to age.

On top of that men of a certain age, tend to have different ideas about how to treat women, not always, but sometimes it may be a problem if you would prefer to maintain your Independence. Just trying to say that it's worth remembering that he grew up in different times where it was ok to treat women in a way that it usually isn't nowadays.

If I remember correctly, I think the largest age gap that I've dealt with in a relationship was only 6 or 7 years. Even with that gap we had a hard time talking about things like music, movies, and politics. I constantly had to remind myself that, well, of course she doesn't remember that, she was in elementary school when that song was popular or when that movie came out, or when that guy was president. I know it sounds like a small thing, but it does have an impact on a relationship. With a 23 year gap, he'll have to remind himself that you hadn't even been born yet.

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    There really are generation-defining moments! The younger set I meet doesn't remember 9/11. They don't remember being scared of the Soviet Union. My older boy -- [pause for shuddering breath] -- said these words to my face, he said, "Yeah yeah, everyone knows Anakin is Luke's dad." The boy understands nothing. That revelation was shattering back in the day... – akaioi Oct 18 '17 at 3:02
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    The question doesn't specify whether the asker is interested in anything long-term. – Erik Oct 18 '17 at 9:47
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    OP states she's interested in older men in general. This happens, for some a relationship with someone that holds quite a different view is totally fine. Some people like to learn from an older mentor or love feeling young again by reliving/re-experiencing things anew through the eyes of their lovely younger partner. – Darkwing Oct 18 '17 at 16:23
  • @Darkwing "I'm not saying that any of these things are deal breakers, or that they should be. They're just things worth thinking about before pursuing anything." – apaul Oct 18 '17 at 16:25
  • While it's okay to point out the potential pitfalls, I think most of what you mentioned isn't specific to older men. You always need to make sure you can trust the other person and there is always a chance you cannot or your hopes and dreams are different. I'd see the "being married" part as the bigger issue. He may just enjoy the nice view or the feeling of a little flirt without having intention on ever acting on it. As long as he's married (and with no indication of some alternative form of relationship) the proper way is not to engage in anything, out of respect for him and his family. – Darkwing Oct 18 '17 at 16:28

You can only get hurt here. Stay away.

Let's look at the potential outcomes:

1. You have an extramarital affair Eventually it will end. (Married men don't leave their wives.) The best possible outcome is that it all stays private, and you don't and up pregnant and you don't end up with an STD (you think you're the only one?), and your friends and family wonder why you're sad.

2. He leaves his wife and marries (or lives with) you Are you ready to be the second wife? The evil step-mom who is the proximate cause of the parents' divorce? The embarrassment that comes between this man and your father?

3. He leaves his wife and then doesn't marry you Everything in #2 except that you don't have to see his kids (who hate you) every other weekend.

4. He leaves his wife and then you don't (want to) marry him Everything in #3 with the addition of being generally despised in the community as a literal home wrecker. This would take years to die down.

"So what do I do?" Avoid this man. He is old enough to know that his subtle flirting is wrong and bad, but he's thinking with his mid-life crisis little head. Yes, he has stirred an infatuation in you. You must deliberately kill it.

Do not go where he will be. If you find yourself in the same place with him, do not not make eye contact. If he makes it, look away. Do not talk to him. Do not brush hands with him. Do not go near him.

When you begin avoiding him he will seek you out. Do not be alone with him. When he asks what is wrong, you will not be able to give him a direct answer because he has made nothing explicit. (That's part of the deniability game.) So be correspondingly vague (bad mood, headache, ...) and move away. Eventually he will get the message. Expect him to become slightly angry and aloof. Do not let it make you feel guilty. He is the one at fault.

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    It is okay if your answer is informed by your moral beliefs, but they should not be a reason to pretend that condoms do not exist. And regarding STDs, would his wife not be at a greater risk? – Carsten S Oct 18 '17 at 21:44
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    @CarstenS I can't make head or tail of your comment. Did you intend to post it on a different answer? – Wildcard Oct 18 '17 at 23:53
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    @CarstenS whether or not the wife is at a greater risk doesn't affect the risk for the OP. (It could be that the man and his wife are not intimate anymore for a longer time.) – Paŭlo Ebermann Oct 19 '17 at 19:49
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    While it is of course good to be aware that sex can lead to pregnancy and infections,I find it quite curious to mention those near the beginning as if they were likely outcomes. That's all. – Carsten S Oct 20 '17 at 1:53
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    One thing to add to the second option: the second wife out of 2 or more. Divorcees are likely to divorce again. – Peter Oct 22 '17 at 12:20

I see two questions here.

To approach a married man you would have to find an excuse to be alone with him. Ask him for his help on to buy/get something that would require his expertise alone. You might have to do this several times since your dad might tag along. That said, this will also give you a probable answer to him being interested in you. If he comes alone (no wife, no kids) he is more probably into you than not. Also listen deeply into if and how many times does he bring her wife,kids and dad into your conversation when you talk to him. Those will be your parameters into advancing into a flirtatious chat. After that just flirt with him as usual.

The second question is more moral/life experience related but ill try to keep those issues aside. Clearly you are into him.

If you truly want only a short term sex relationship you will have to understand your place in the relationship. And this means that by no means you will be above his family or his relationship with your dad as a friend. That mean no dramas over jealousy, lack of time/attention, money, etc. Same rules apply to him. And both must understand that a relationship wont have the deepness of emotional level of even a bf/gf relationship. If you can cope with all of the above at your age and understand the consequences of being found out or an accidental pregnancy, then yes, such a relationship could exists. But i must really stress out that both must play under those rules to minimize any problem that might arise and cause unhappiness to either side and to be ready to end that relationship at any moment.

If you want a long term relationship then the answer is No. Too many problems starting from age gap, cheating, awkwardness with your family and probably damaging your relationship with them. You are too young to deal with a family building relationship with a guy with that background. At your age, probability states that you will find a less troublesome prospect for a boyfriend.

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    Solid and balanced advice @Salvador Ruiz Guevara -- I appreciate and upvote! – English Student Oct 20 '17 at 5:29

You don't....If he's Married then you would be a homewrecker, If Vic wanted a relationship Vic needs to decide his present relationship. And then there is your father, they are friends, don't mess up their friendship for lust. The Butterfly effect can come back to make you regret what you may not be wise about now. If Vic is married then Vic is not on the market, find somebody you probably was destine to find. Lust never turns out the way you planned.

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    "He is old enough to know that his subtle flirting is wrong and bad, but he's thinking with his mid-life crisis little head." __ that makes too much sense @Amber Hart! – English Student Oct 19 '17 at 0:22

You're strong, intelligent and mature as anyone, if not more. Now, my answer to your question would be : be careful. First, you cannot know for sure he is interested in you so try to make it clear that he is. Second, be discrete cause he is your dad's friend, if your dad catch you with him he might get angry. Third, try to know more about his family life. If his marriage is already unhappy, you won't be responsible from wrecking it.

My advice is to be careful and take your time to make sure you don't get involved in an embarrassing situation. I wish you the best in your attempt at fulfilling every teenager's dream.

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    "If his marriage is already unhappy, you won't be responsible from wrecking it"... I can't disagree more. That's like standing over someone who is lying on the ground after being shot several times, pulling out a gun and putting a bullet in their head. Then saying "I'm not responsible for their death, they were going to die anyway". – Matthew Snyder Oct 22 '17 at 20:20
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    @MatthewSnyder Are you saying that OP would be responsible for Vic cheating on his wife ? I'm sure he's mature enough to say no if he doesn't want to, and if he says yes it either means that is has poor morality or an unhappy marriage. In both cases OP isn't responsible for "wrecking his marriage" which only concerns Vic and his wife and not OP, as she isn't part of their relationship. – F. Emin Oct 23 '17 at 14:36

Try to flirt with him online, on facebook/whatsapp/whatever. He doesn't approach you because it could be dangerous for his reputation if you reject him and tell everyone. (look at this ton of judgemental comments, even here).

As soon as he realizes you really actually like him, he'll make steps too. At that point, you'll need to decide if you both want to be secret friends with benefits (doable) or have an actual relationship (a little harder, will require some guts from you both to withstand the pressure).

  • This answer seems to operate under the assumption that he is definitely interested in some sort of relationship. I'm not sure how we can get there from the information in the question. – JMac Oct 18 '17 at 18:41
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    In case he's not interested, it's very unlikely a 44 y.o. man will hold any grudge against a 21 y.o. girl just for flirting with him on facebook. – Ivan Skalauh Oct 18 '17 at 20:31
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    Amazingly, the only answer to actually give a sensible answer to the actual question. And it's being downvoted. – pipe Oct 19 '17 at 14:05
  • @pipe fair comment, though it is appropriate for answerers to say "Hey OP, I think you may be making a mistake here..." People come here and give answers because they want to help people. Sometimes that includes questioning the premise of a question, that's all. – akaioi Oct 20 '17 at 5:27
  • This post was discussed on meta: interpersonal.meta.stackexchange.com/questions/1940/… – apaul Oct 20 '17 at 5:54

Thanks for updating your question, with that information I have something to add.

How do I ask my dad's friend if he's interested in me?

There is no reason to ask him if he is interested in you: he is. At the very least, in your appearance. You are also interested in his appearance.

At the heart of it, his behaviour is making you uncomfortable. He is checking you out quite blatantly, encouraging your own feelings of attraction and reinforcing a sexual chemistry between the two of you. There would be only two reasons for you to approach him about his apparent attraction to you:

  1. You want him to stop checking you out
  2. You want to act on this mutual attraction

(The third option is not to ask him at all, which I’ll get to at the end).

I think the other answers have gotten into the second option (whether or not to act on it) well enough, personally I agree with English Student. You need to think about the effect it would have on you, your family, his family and the relationship between the two families. If you do not want to be a homewrecker, you cannot act on it. Tempting as it is, it's that simple. Is it worth it? Only you can say. Personally, I wouldn’t go near it.

I’ll talk a bit more about the first option: asking him to stop. If you decide against making a move on him, you are still left with the fact that he stares at you and it bothers you. I think again there are two ways of dealing with this:

  1. Truth: Telling him the attraction is mutual, but you’ve decided against acting on it, and request that he stops staring because it’s inappropriate and makes you uncomfortable
  2. Lie: Telling him the attraction is NOT mutual, and request that he stops staring because it’s inappropriate and makes you uncomfortable

First, let me just say: it can be incredibly difficult to stand in front of a person who you are attracted to, hear them declare that they are also attracted to you, and decide not to do anything about it. Even if he has the same reservations as you, it is going to be tough. If he doesn’t, he might be able to sway you into acting on it. Even just having it out in the open might escalate both of your feelings and end up swaying you. This first option is tempting, and it’s honest, but it’s a rabbit hole. I really wouldn’t recommend this unless you have superhuman levels of self-control.

For that reason, if you really feel the need to say something, I think it’s best to go with the second. You would need to deny outright that the attraction is in any way returned on your end and keep the conversation short and to the point. That’s also going to be incredibly tough. Again, he might attempt to sway you. You need to be able to hold your ground. Again, superhuman levels of self-control needed. It’s possible he’ll just accept it, apologise, and you both move on … but since there’s no way to know how he’ll react, it’s a pretty big risk.

I just want to know if talking to him/responding or reciprocating his flirtations are a good idea.

No, I don't think it's a good idea.The third option is to do nothing. It seems like a bit of a cop out, but IMO it’s the best course of action. It’s so tempting to go down the rabbit hole on this one, to bring it out into the open and see what happens, but you need to make your decision and stick to it. In this situation, any action you take is putting you on a slippery slope.

My advice is to stay out of it, don’t verbalise it, and stick to your daydreams.

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    Solid answer and your advice is most comprehensive for OP, thanks @sudowoodo. In all the famous romances the heroine goes to tell this 'mysterious charming person' that she is not attracted to him and then and there one thing leads to another and the opposite result occurs, followed by conflict, heartburn and an infant child after 10 months with the mysterious stranger nowhere on the horizon. Times have changed but human responses remain the same, so you are very right to tell OP to resist temptation and do nothing. Also, wise people have historically counseled: when in doubt, do nothing! – English Student Oct 20 '17 at 6:13

protected by apaul Oct 19 '17 at 16:06

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