I've made a friend, Bob, in my workplace who is too much of a gentleman for my comfort level.

Initially, we became fast friends due to our shared interests and political beliefs. We often message outside of work and get lunch together every few weeks. We don't work in the same department, so these lunches are usually the only times we see each other. The problem is that Bob's acts of kindness are making me more uncomfortable as time goes on. I haven't told him this yet.

Every time we go to lunch, Bob always rushes over to my side of the car to open my door for me. I've told him he didn't have to do this, but he insists that it's "the way his mother raised him" and does it anyway. He also always pays for my meal, even when lunch is expensive. I've went as far as asking the waitress for two checks, but Bob will catch her a moment later and ask her to go ahead and put everything on one check. I've explained that I don't want him to feel the need to pay for my meal, but he continues to do so anyway.

While I'm totally fine with the actions themselves, the combination and insistence of these two habits make me uncomfortable because I do not want Bob to be doing this as a romantic gesture. I also don't want to alienate Bob, because I rather enjoy his friendship. As is, though... I'm starting to find myself wanting to avoid Bob so that I don't have to worry about his intentions every time I eat lunch with him. I don't know if he does these things for other women.

I'd like to get Bob to stop doing these things for me without making myself look presumptuous, unappreciative, or making Bob feel bad on the off chance he isn't trying to "woo" me with these niceties.

What can I say/do to kindly show Bob that I prefer to do these things for myself?

Note: I have a partner - and I haven't told Bob directly, although he may know through my posts on social media - but for various reasons I'd like to deal with my situation with Bob without using my relationship status as a crutch.

We're both white Americans from the Midwest United States.


12 Answers 12


The potential romantic angle is a red herring. Whether or not Bob is interested in you and intends these gestures to be his "moves" on you, you don't want the gestures at all because they suggest that he might harbor those intentions. Him denying romantic interest probably wouldn't resolve this (would you believe him and then become totally fine with the gestures? Or would you always wonder, at least a little, and continue to have the same problem?). I know plenty of women who, even when on explicit, romantic dates, vastly prefer to do things themselves (particularly paying for meals). So from my perspective any mention of Bob's (possible) romantic intentions are already off-topic and cannot be of much use to you in achieving your goal.

When it comes to actually stopping these behaviors, you should be clear, direct, and ready to back up your preference. You strike me (from this question and elsewhere on SE) as someone who prefers more indirect communication, which can be easy to misinterpret. Consider

I've explained that I don't want him to feel the need to pay for my meal, but he continues to do so anyway.

If his impression is that he shouldn't feel he needs to pay for your meals, that suggests that he still can if he wants to. Since he's trying to be a gentleman he may well still prefer to do so. In his mind he may be even more of a gentleman for it because he's doing it by choice rather than obligation. Conversely, if you expressed to him that you do not want him to pay for your meals, there can be no question that he's going against your wishes by paying. DO NOT expect him to just "get the message" somehow, especially as there seems to be some chance that these really are his default behaviors.

When I say back up your preference I mean declining to spend time with Bob if he maintains these behaviors despite your clear and direct request that he not do so. If you like, you can explain that you feel uncomfortable when spending time with him due to these gestures. That makes it clear that his choices are to stop spending time with you or to stop the rote behaviors.

All you really need to say is something like

Bob, I appreciate your being so attentive to me. But it really makes me uncomfortable when you do things like this, and I don't want to be treated this way.


It sounds like you're looking for a gentle, yet direct approach that will level the field without making him feel snubbed or put off... So, why not word it that way?

It'll probably help to set the stage before you're already on your way to lunch:

Hey Bob, I appreciate your old fashioned gentlemanly way, but it feels kind of unequal by today's standards, it's 2018 after all. This time I'd like to drive and pay, and in the future I'd prefer to pay separately.

Placing things in an equality, or feminist, frame may get him to relax on the "chivalry" and it may neatly avoid an uncomfortable conversation about your relationship status.

Although it doesn't really address the suspected underlying problem. If he's really being "chivalrous" in order to court you, which isn't really chivalrous, you'll probably need to be more direct. You can be direct, while also keeping the tone light with something like:

Hey Bob, I appreciate your old fashioned gentlemanly way, but it feels kind of unequal by today's standards, it is 2018 after all. This time I'd like to drive and pay, and in the future I'd prefer to pay separately. I can pay my own way, it's not like this is a date.

Using a light, almost joking, tone allows him to save face and hopefully he'll take the opportunity "Of course this isn't a date, we both knew that, haha..."

  • 16
    "it's not like this is a date" - putting someone in the position of needing to deny something is generally more awkward than putting them in a position to agree with you. I might suggest something like "I mean, we are just friends, after all" instead. Also, a light tone might be interpreted as "I would never date you", so that might be best avoided.
    – NotThatGuy
    Commented Sep 26, 2018 at 12:09
  • 3
    @NotThatGuy This would be putting him the position to agree that it's not a date...
    – apaul
    Commented Sep 26, 2018 at 21:20
  • 2
    I wouldn't use the word prefer, as it still makes the decision his as to whether he will allow his own preferences to overrule your preferences (s/he doesn't always want to pay, she just prefers to). I would say polite and direct would be preferable to being vague, and leaving the door open for further problems.
    – NibblyPig
    Commented Sep 27, 2018 at 10:17

I think you’re probably right about not relying on the existing relationship, as that’s not in-and-of-itself the reason you are uncomfortable with this behavior. It would be inaccurate, and can cause anguish later if, as a worst-case scenario, your relationship status were to change. And frankly, it’s not his business why you are uncomfortable with his behavior; you just are.

(For what it’s worth, totally with you there: it may well have been how he was raised, but frankly I’m not buying it—holding the door for someone is one thing, but running around a car to get the door is something else, and paying for lunch is another level beyond that. Personally, those are things I do as romantic gestures for my wife. It has been quite a while since those were considered the expected behavior of a gentleman with every woman. Certainly a rather patriarchal form of chivalry, even assuming that isn’t an inherently redundant statement.)

Also, there is a technique in many kinds of communication wherein you intentionally refuse to offer explanation. Offering explanation invites discussion or debate, possibly counter-points or what have you. Talk about exactly what you certainly don’t want! So I also think you are simply better off avoiding an explanation, whether that be your existing relationship or any other.

So I think you are best off just putting your foot down, so to speak. No explanation, no excuses (for you or for him), just a plain statement. No need to make a big deal about it, you certainly don’t want or need to guilt him for anything he may or may not have meant by it, but it should be clear. I would start with the paying-for-lunch thing in particular: it may not be very much for him to open the door for you, but paying for you is explicitly costing him money.

I would suggest something like,

Please, really, I am not comfortable accepting your money.

If he insists or pushes, I suggest saying exactly what you have here:

No, really, this is uncomfortable and it makes me not want to get lunch with you, knowing you’re going to make me uncomfortable. I won’t keep doing that.


As you have mentioned in comments that you have not told Bob that this makes you uncomfortable (and why), I suggest you do so.

  1. I would recommend explicitly telling him to stop the behaviors that are bothering you, and would note that "You don't have to do this" is not, strictly or even generally speaking, telling him to not doing something. It is telling him that he is not under an obligation to do something. For example, if I get into the office earlier than my coworkers, I would set up the coffee maker and start of coffee for the office, so that it would be ready when my coworkers arrived; this is not something I had to do, as it wasn't in my job descriptions, was not asked of me by my superiors, and I don't drink coffee. Multiple times, my coworkers have told me "I didn't have to do this"; no one ever told me to stop, until the office got a Keurig machine.

    I also would recommend specifically naming the behaviors the , rather than asking him generally, e.g. to "stop the chivalrous behavior".

  2. While I agree with OldPadawan's comment, that being told that his actions make you uncomfortable should be sufficient to make him stop. However, since you are friends, and if he stopped these behaviors the two of you would presumably continue to meet for lunch, and you don't find the behaviors inherently offensive,I would recommend telling him your reason for disliking the behavior, namely that you think it is being done a romantic gesture and you wish to keep your relationship platonic.

  3. Seeing as you asked for what to say, I would recommend saying something like this (removing anything that isn't true): "Bob, I enjoy being friends with you and eating lunch together, but your habit of constantly opening doors and paying for my food (and any other behaviors) are are making me uncomfortable. Please stop with these romantic gestures, or we'll have to stop having lunch together and I quite enjoy your company".

    It is quite possible for Bob to deny any romantic feelings; in that case, I suggest you accept his denial, but state that it still makes you uncomfortable and re-iterate your request that the behavior stops reguardless.

    I wouldn't worry about alienating Bob; either he is a good friend, and is willing to drop the behavior for the sake of your comfort, or he is not someone you want to be around, and you are exiting a bad situation early. I agree with jcmack's answer that frankness is generally appreciated.

  4. Personally, the check behavior is more egregious because a) it involves money and b) he is countermanding your actions and intentions. Therefore, I would focus on this behavior more.

  5. Finally, as a man who also had this sort behavior pounded into him by his mother, and for whom it also caused problems, I would request that if you ever have sons, that you "pay it forward" and not impress this behavior upon them.


I think you need to distinguish some of his actions, and temper your reactions to them.

Opening the door for someone is just a polite gesture, not related to any kind of romantic interests. As he said, it's just how he was raised, and I think you should let this go. It can be a hard habit to break, so just view it as one of his ideosyncracies. If you want to keep him from doing it, you just need to be faster at getting out of the car.

On the other hand, paying for a meal is generally considered part of dating. Platonic friends rarely pay for each others' meals, unless it's regularly reciprocated -- one pays one day, the other pays the next time, etc.

You need to explain to him that you consider yourself a modern, independent woman. When he pays for you, it diminishes your self-esteem. While you understand that he doesn't mean anything demeaning by it, that's still how it feels to you. Maybe you can try to get the server to give you the check, so that you can pay sometimes. When they're coming to the table, grab the check and say something like "It's my turn this time."

Perhaps the next time you're arranging to go to lunch, you can say "I'll only go if you let me pick up the check". Once the water has been broken, maybe you can get into the reciprocating rhythm I described above.

If none of this works, I think you may have to put your foot down and cut off the relationship with him. I know you say you generally enjoy these occasional get-togethers, but if he does something that really annoys you, this may be the only way for him to get the message.


What can I say/do to kindly show Bob that I prefer to do these things for myself?

Female poster here. I have encountered this situation, and these are the different steps that I usually take.

1. Expressing my needs clearly.

"I've told him he didn't have to do this"

"I've explained that I don't want him to feel the need to pay for my meal"

This does not express the fact that you are not comfortable with the situation. It can be misinterpreted as "You don't have to do this, but if you want to, please do".

Saying, unambiguously:

"I have the means to pay for myself and would like to do so. Not paying for my meals makes me uncomfortable."

will be enough for some colleagues. For the rest, see step 2.

2. Explaining in detail why it is not OK

Here are different reasons I used.

"Having you pay for my meals makes me feel uncomfortable because:

  • it introduces an imbalance of power in our relationship if you always pay, it makes me in your debt, and that is not OK

  • since you do not do it for every colleague you eat with, it is favorable treatment, and thus not professional behavior. It could be misinterpreted at the office and I don't want it to start gossip.

  • we can't have gallantry and gender equality, I'd rather have equality

At this step, most people understand and stop it. That being said, I had some people answer that "This is a matter of education", or "You are not in my debt because I gladly do that for you without expecting anything", or "It can't be misinterpreted because I am married", and for those cases, I offer point 3.

3. Doing exactly the same thing they are doing

Here, we are no longer in the "nice part" of the advice, but that actually worked really, really well on all extreme cases of people not taking no for an answer:

  • They rushed to open the door in front of me, I did the same and rushed to hold the door
  • They insisted on paying for all meals, I jumped on occasions when they would go for a smoke or to the bathroom, and so forth to pay for the whole meal.

After a couple days, it made them really uncomfortable. One was feeling stupid making a scene each time I paid, one was just feeling in my debt and being uncomfortable about it, ... This is when I explained that this is the way they make me feel, and it usually made them stop.

I, at the moment, haven't had one guy on which that last part did not work, but you have to stand your ground and be very firm about it. Good luck.


From a psychopathic and removed perspective, all relationships (Romantic or otherwise) are about value. The only reason you spend time with him is because you get some value from the relationship. I would say that in his case he feels as though without doing those things he feels less valuable.

Regardless the intent of the actions however, you do need to be careful if you wish to maintain the relationship.

Be blunt and straight forward that the actions make you feel uncomfortable. DO NOT relate them to romantic or really even mention his intent. Because an assumption about the intent, if wrong, will drive a wedge between you two, and if right, will drive a larger wedge between you.

Essentially his intent should not be of your concern, nor should it affect your decision making. You choices, how you feel about the situation and ultimately what you say to him should be based of your personal feeling about his actual actions.

You need to tell him that his ACTIONS make you feel uncomfortable. (No need to qualify with a reason, and definitely do not go down the gender equality route suggested in another answer). If he asks you why they make you feel uncomfortable, your best route is to target the paying for food. Say you dislike always depending on him, and suggest a solution (Maybe take turns paying).

Whatever you say, give a solution, and make it clear that you value his company, not him paying for things for you. He needs to understand that you genuinely like spending time with him, but are currently uncomfortable because of his over the top actions.

  • Good answer, although I suggest ignoring the bits trying to guess the intent whatsoever.
    – user10743
    Commented Sep 26, 2018 at 14:33

TL;DR: "Bob. It's not going to happen. But thank you very much."

Speaking as a man who has been gleefully guilty of this, I would suggest that you do not have a friend in Bob -- not the type you want, or that he wants -- and you have nothing to lose but an illusion. This undefined zone of discomfort is as close as you are going to get to a mutually satisfying relationship. That is why neither of you have changed it. You both know what's up, and you are both hoping for the other to come around. It's not going to happen. This is a politely prosecuted pursuit/evasion relationship, and it will feed on itself without fundamental change.

I believe that even in your question, "What can I say/do to kindly show Bob that I prefer to do these things for myself?", you are politely avoiding the real issue. Bob knows that you would prefer to do these things for yourself -- but he would prefer to do them for you. He is placing a marker for later, while simultaneously defending his territory against other comers. He has reserved you for the future, and wants everybody to see it. Door or no door, you have expressed that you do not wish to be reserved for the future.

It sounds that you and Bob have a relationship which can survive a bump. I suggest a gentle, caring, forceful statement in a place of sufficient privacy to respect his needy ego: "Bob. It's not going to happen. But thank you very much."

There won't be much need to explain, or even to continue talking. It will be what it will be. Bob may in fact not be able to deal with this very well going forward, and will probably be angry, humiliated, and distant for a while. That's just a wounded ego. But you're already in a dreadful situation, and frankly, so is he.


There are a lot of good answers here, but i wanted to answer from the other side of the fence. I know my situation is not exactly the same as the OPs but i thought it might offer a small amount of useful insight into how Bob feels in this situation

My Situation

I was raised in a similar way to Bob, that the gentlemanly thing to do is to drive and pay for dinner/drinks when out with a woman. now this extends to both my girlfriend and to other woman on the very rare occasions i go out with a colleague or an old friend without my GF. now this is an ingrained behavior; i appreciate it is not in keeping with Feminism or equality standard of today, however it is still something that i feel strongly about, as i said its how is was raised.

Other Women

For a moment we'll ignore my GF and come back to her later. i'll start with a couple of female friends, I know that they are independent women and like to make their own way, but when they pay i feel i'm letting them down. I KNOW this is not the case but it is still the way i feel. and that uneasy feeling those few women may have which as similar to those feelings of the OP are probably about equal to the uneasy feelings I have when they pay. there is no romantic intentions between myself and these other women but the gentlemanly feelings are still there.

Most of the time my friends know its just how i am, and agree to let me pay for the meal, however if we go out of an evening to the pub, they will always push past nad pay for drinks before i get a chance to get to the bar, this frustrates me but they've informed me that if i'm not going to let them pay for lunch then they're buying rounds!!!

This simple friendly almost jovial but firm stance left me with two choices:

  1. Ignore them and demand to pay, which in itself went against my gentlemanly mindset as ignoring them or going against their firm wishes is outright rude
  2. suck it up and let it happen

I know this makes me sound bad, but after some time and many occasions like this when the women suggested grabbing lunch, we went and when it came to paying they would say "No, i'm paying my half" i would allow them to do so. they always did this politely and without anger in their voices but were firm about it.

The thing is i'm still uneasy each and every time it happens, if Bob was raised in a similar many to myself then he will never be happy with the situation so ingrained is this mentality, but he may be willing to accept it

My Missus!

Yes i know this is not the same situation as its between partners in a Romantic relationship but... the methods she has taken to break my habits in this regard may be of use. my GF is a fiercely independent woman, but due to an eyesight problem is unable to drive, so we'll ignore driving from this.

Myself and my GF often go out for lunch or dinner, (rarely anything posh its usually just pub grub) when we first started dating this actually caused some friction between us as she wanted to pay for dinner or at least half of it and i wanted to pay in full. so she began a campaign to break my gentlemanly habits, it began with:

  1. If i left the table to use the facilities or go for a cigarette (Yes i'm a smoker, yes i know its unhealthy) she would get the bill while i was away from the table.
  2. She would suggest going out for dinner but only under the condition that she be allowed to pay
  3. She would book activities which could be paid for in advance and then any difference at the end i was "allowed" to cover

These days if my GF says she's paying then i no longer argue, i don't try to pay behind her back, I accept its her choice despite how uneasy it makes me feel.

If she leaves it open however then i'm going to pay!

Opening Car Doors

This is the exception to the rule. opening or holding open a door for someone is something i will always do if able to do so, and quite frankly i will not stop it, its only meant as a polite gesture. i will admit i don't go running around to the other side of the car as quickly as i can though. if they get the door open before i can, then i can't exactly stop it can i?

Edit as per a comment:

I'm not suggesting you or anyone should feel sympathy for Bob, although i understand how this answer might read that way. Just that the automatic assumption that Bob is definitely acting this way because has romantic intentions is incorrect. its possible of course but it could be something else and may explain they way he acts which are not always obvious.

I was further detailing my feelings to explain why my missus and others had to use the methods they did in order to "break my habits" I knew i didn't need to do those things but "i was just being nice so why was anyone getting annoyed" was very much MY mindset until proved otherwise.

Final Thought

I appreciate this final section will likely attract downvotes but: For the OPs sake i hope they can convince bob to calm his conduct without causing offence or embarrassment to either party, but if Bob is truly just being a gentlemen without other motives as the OP suggested is possible, then i hope they can find a middle ground where neither feels uneasy as to the way their lunches etc go

  • 6
    I don’t think you intentionally implied this, but it’s there anyway so I hope you’ll consider rereading and editing your answer with the following in mind: This rationalization makes it seem like others should feel bad for denying a “gentleman” control over their own actions. For a man to refrain from holding a door affects only his own psyche, but to expect others to acquiesce means they have to change their preference for someone else. That is a problem.
    – user10743
    Commented Sep 26, 2018 at 14:17

There are a wide range of answers already but if you believe it is due to romantic intent, I'd go directly to shutting that down.

Explain that [gentlemanly actions] are things you only feel comfortable doing with a romantic partner and thus you don't want to continue them as you feel uncomfortable.

Gentlemanly actions being stuff like, him paying, him opening the door etc.

This would shut down any romantic play completely.

Edit: To answer the comment below...

You need to know what the guy's intent is, and most likely in this situation it is because he harbours romantic feelings. Although the OP doesn't state this explicitly, I would assume it is as it's a common scenario especially with someone being so generous to another - the behaviours he exhibits are very unlikely to happen between two heterosexual males for example. His behaviours are therefore romantic in nature and the only way to stop him from performing such behaviours is to demonstrate that no romantic connection exists or is possible. Many other answers involve directly explaining the symptoms (the manifestations of his romantic intent), saying that they makes the person feel uncomfortable but this does not address the root cause. Without addressing the root cause the person will find other ways to express their romantic intent, and the problem will persist.

Therefore it is required to shut down the romantic intent, either directly or indirectly. The direct approach, akin to saying "I like you but I am not attracted to you" would result in hostility, because the guy has never explicitly stated romantic intent and therefore would be upset at the presumption. So an indirect approach would be better. However it needs to be an approach that leaves no room for things to change or for ambiguitiy, and also if there actually is no romantic intent doesn't jeopardise the relationship.

Therefore stating that you don't feel such gestures are appropriate outside of a romantic relationship, you have clearly stated there is no romantic relationship or accord between the two of you. OP said not to use their own relationship status but I think it would help to add that in, by saying such gestures are appropriate outside of a romantic relationship like the one with my husband. This would help neuter the idea that a romantic relationship could possibly form in the future.

It also expresses the fact you're uncomfortable with any kind of gesture as opposed to stating which gestures are inappropriate directly, and doesn't use words like I would prefer... which suggests there is some flexibility.

Lastly it doesn't hurt the guy's feelings as much because you're not outright implying there is anything romantic going on.


What can I say/do to kindly show Bob that I prefer to do these things for myself?

Exactly what you told us, in firm but friendly terms. As you are friends, this should be possible without alienating him. If it does not work, then you have a pretty good indication that it was not "just" friendship or old habits that were driving him.

I'd go so far and make this the first topic of one of your lunches...

Hey Bob, there's one thing that I need to bring up. I've found out that your two habits of opening doors for me, and paying my lunch, make me really uncomfortable to the extent that I catch myself not wanting to go to lunch anymore. You have already explained to me that those are habits of yours.

Please, accept that I these are not my habits, and that I am really unhappy whenever you do it. Please do not do it again, as it destroys the whole lunchtime for me.

Of course, word it as you would usually talk, and be happy and cheerful. No "sorry", no "you do not need to...", just a simple, clear message. And get any thought of hidden agendas he may or may not have out of your head.

If he keeps explaining that you do not need to feel unhappy about it, then repeat that you do feel unhappy about it, and add that it would mean a lot to you if he respected that wish of yours.

There is no way whatsoever, if you keep repeating that thought in the discussion, that he can talk his way out of it - you keep repeating that he is making you uncomfortable and that you would like him to respect your wish, that you do not want it, that you do not want him to force it on you, etc. If this takes a lot of talking, or if you cannot get through to him at all, then maybe you should rethink the friendly relationship you have going on, after all.


Note: I have a partner, but for various reasons I'd like to deal with my situation with Bob without using my relationship status as a crutch.

The best way to spare Bob's feelings if he were romantically interested in you is to indicate that you are already in a committed relationship. This isn't a crutch so to speak, but pretty clear way to indicate "If you're doing this in a romantic way, it's not going to get you anywhere."

Personally, I would recommend a frank conversation with Bob and about how his chivalry makes you uncomfortable. For instance, you feel like the gestures are more appropriate for your significant other or that you feel you fully capable for opening your own doors and paying for your own meals. A true gentleman/person does acts of chivalry not because the other person is incapable of the action, but that they feel as though they shouldn't have to.

I've had a friend confront me with the same question making sure my gestures weren't coming from a romantic angle. It didn't ruin our friendship or anything (I wasn't coming from a romantic angle), and I appreciated the frankness.

  • 15
    Are you sure that this is the best approach to heading off romantic intentions? The preexisting-relationship angle implies "... it's not going to get you anywhere, because I [OP] am in a relationship right now." This can then further be 'optimistically' interpreted as "Otherwise, things would be different" and I believe this is what OP is trying to avoid. Commented Sep 25, 2018 at 21:51
  • 1
    @spiralsucculent That's not how I would interpret it and frankly that's reading way too much into it. It's like saying to a vegetarian "Here is a hamburger." and vegetarian responds "I'm a vegetarian." Does it matter if vegetarian is thinking they'd be all over that burger if they weren't vegetarian at the moment or that all meat is disgusting all the time? Either way, they don't want the burger now. Same with the OP not being into Bob right now. Pursuing someone that is already spoken for isn't gentleman/person-like behavior anyway.
    – jcmack
    Commented Sep 25, 2018 at 22:22
  • I'd be happy to discuss further in chat chat.stackexchange.com/rooms/61165/the-awkward-silence Commented Sep 25, 2018 at 22:27

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