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

Question

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!

Answer 1

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.

Answer 2

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.

Answer 3

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.

Answer 4

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.

Answer 5

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.

Answer 6

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.

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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.

Answer 7

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.

Answer 8

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.

Answer 9

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.

Answer 10

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.

Answer 11

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.

Answer 12

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).

Answer 13

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.