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DearSugar Needs your Help: Should I Stop Accepting his Gifts?

DearSugar and Greedy Gretta need your help. An older man has been showering her with expensive lunches and flowers yet has never made any advances on her - should she assume that they really are just friends, or should she vocalize her concerns and implement some ground rules?

Dear Sugar--

I went out one night with some girlfriends and we met this really nice, charming older man. He took a liking to me specificially and ended up paying for our entire night out (it wasn't cheap, let me tell you). We have since gone out to lunch a few times and he always picks up the tab despite my offering to pay. Last week, after one of our lunches, I came back to work to see an enormous bouquet of flowers on my desk from him, and the card read, "Thank you for yet another wonderful afternoon." I was extremely flattered but then started to feel really uncomfortable with our relationship.

Now I know what you are all thinking, he wants to get into my pants, I am using him for his money, but that's not the case at all - he has never once made a move on me, we enjoy each other's company, we laugh together, have intelligent conversations about art and politics, and we seem to be on the same page about life, but now I am starting to think he wants more from me. But then again, what if I am wrong? What if he generally likes my company and doesn't want anything more? Should I stop seeing him? Should I tell him the flowers made me feel uncomfortable? I am torn because I don't want to accuse him of being interested in me if he isn't and then I will feel like the stupid one. Has anyone ever been in a similar situation? HELP!

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Elle-Tea Elle-Tea 8 years
Although I think it's likely he is interested in a romantic relationship with you, there's no need for you to break off contact with him. I would suggest saying something along the lines of, "I really enjoy our friendship and would hate to jeapordize it, but I want to make sure you understand that a friendship is *all* I am interested in." He may decide that if there's no hope for more, he's not interested, or he may decide that he enjoys your company enough to remain friends- either way, you should let him know where you stand so he can have a choice.
paulinhadrp paulinhadrp 8 years
I think you could be very innocent. I do think he his interested from what you have said, and if you are not interested at all, let him know how you feel before this gets even more uncomfortable.
tralalala tralalala 8 years
talk to him if you feel guilty about it, otherwise, just go with it! A lot of older guys genuinely just like to spend their money on pretty girls, my old roommate pretty much made a career out of it haha. As long as you don't lead him on, there's nothing wrong with it
Melissa55 Melissa55 8 years
While it is rare that men will spend lots of money on women they are just friends with, it isn't totally out of the question. You just need to be blunt and say "You are confusing me, where do you think this friendship is going?" Hopefully, he will answer you honestly. If he doesn't, then obviously you don't need him as a friend anyway. Secrecy and manipulation have no place in true friendships, no matter how good the conversation is.
jennifer76 jennifer76 8 years
All you need to do is make your own intentions clear. I had an older man at my old job who would always bring back gifts from his travels for me. And he'd buy lunches, etc... He didn't have a wife or children and he had way more money than he needed. He just really liked to be able to share that with somebody. He never once made a move on me and my husband (then, boyfriend) and he got along very well. Tell him that you're concerned and don't want to give him the wrong message but that you enjoy his company and your relationship as it is. You'll probably find out that he's just a lonely guy who likes to do nice things for you.
maggieNZ maggieNZ 8 years
You so know the answer to this. Even if you confront him, he will tell you he doesnt expect anything and he understands you are just friends. Pfft. He may not expect anything to happen, but he definitely wants it to, and he's trying really hard to make it happen, plus if you end up seeing someone else he definitely wont like it and you will feel guilty and torn. Either start dating him, or end it now. Good luck! :)
junebrug junebrug 8 years
Um, duh. Maybe because this has happened to me, it seems so obvious. OF COURSE he's interested in you. He knows his youthful good looks aren't going to hook you, so he's hoping his money will. He hasn't made a move yet because he doesn't want to scare you off. When I thought I was "just friends" with a much older man, I had to logically ask myself, "What on earth do a 30 year old woman and a 60 year old man have in common?!" We weren't actually "friends" for a moment, I deluded myself into thinking it was okay. Modern times is responsible for most of this: we're taught nowadays that men and women can be friends and we don't want to presume. I swear the modern world have put blinders on all of us. He's interested. If he's young enough to be handsome and appealing, I don't see any reason why you shouldn't date him. And the gifts he's given so far, like dinner and flowers, are inexpensive, and require nothing but a thank you. But if he comes on board with jewelry and vacations, more will certainly be expected of you. I'm not saying this is right or feminist or anything else, but this guy is from a different era. Just so you know, 90% of the women in L.A. would give their left arm to be in your position! However, if you really just are not interested, hanging out with him is not going to work. He wants you, and either you're interested or you're not. Continuing to accept gifts, particularly expensive ones, if you're not interested, is dishonest at best. Be clear with him and stick with it, if for no other reason, because it's the ladylike thing to do. Think karma.
doctor_doctor doctor_doctor 8 years
I have been in this situation a few times, and the best advice I can give you is to come out and ask him, straight-up, what his intentions are. He may just be 'taking you under his wing' so to speak. On the other hand, he may be skhy in communicating exactly what he wants. In the end, if the two of you can come to an understanding (there's no chance of anything beyond friendship, and that you are willing to pay for lunch/acitivities) there's no harm continuing this type of friendship. I have had a few friendships that came from a person expressing genuine concern, and just wishing to do something nice with the scads of money they had. One of these friendships came to me at one of the hardest times of my life, when I was juggling a premedical course load, filing for divorce, preparing to move to a city 2 hours away to attend a bigger college, and involved in a long-distance relationship. Be careful in your decision! GOod luck. :)
demeter demeter 8 years
EXPENSIVE lunches and flowers should be the giveaway for you. You need to stop accepting his gifts, it is completely rude if you don't. I'm pretty positive he wants to be more than just friends with you and by accepting his gifts, you may be making it seem like you are okay with that.
herjoiedevivre herjoiedevivre 8 years
don't keep him longer, please- if you do and he finally makes a move and you rebuff, he'll interpret it as you enjoying your 'free lunch', even though all of his gifts, etc. were totally voluntary. it's just how guys are- don't give them an excuse to bitch about how "awful" women are. tell him straight up that you cherish his friendship and would like it to remain as such, and that you really, REALLY appreciate the gifts and such, but that that's crossing the line. no one sends you flowers thanking you for a lovely afternoon if they're not slightly enamored. that has counted as courting for years. do him a favor and clarify your feelings.
ffifyfofum ffifyfofum 8 years
i think he likes you. like a bit more than a friend. maybe he thinks that you don't want to be more than just friends. i say keep him a bit longer. (besides, he's paying for your stuff)
rubialala rubialala 8 years
I'm with JessBear, and if you don't want to date him, then I will!!! Just kidding, but only cuz I'm married. But he sounds like quite a catch. Think about it.
Marci Marci 8 years
I think the key thing here is that he hasn't made a move on you YET. It's coming, believe me. If you're not interested in getting into anything with this man down the road, don't accept the gifts. But there is no such thing as a free lunch -EVER.
lickety-split lickety-split 8 years
i don't think we have enough information here to say what his true intentions are. how old are you, how old is he, what is his sexual orientation, is he divorced, widowed, has he lost a daughter that maybe you remind him of? i worked with a guy in college that had an older woman take a liking to him. one day after months of just stopping by to say "hi" to him and him being unsure of what she wanted she brought in a picture of her "one true love" and showed it to him. she thought he looked and spoke just like her long lost love and it made her happy to sort of relive the feeling of being "with" him. ask about his family, maybe that will give you some more clues :) hopefully he's just very sweet and it's an unusual but sincere friendship.
rosey_y rosey_y 8 years
He wants you. End of story. :)
JessBear JessBear 8 years
Okay, I have to ask- why AREN'T you interested in him? You say you have intelligent convos, make each other laugh, enjoy each other's company, AND are on the same page in life...I mean, that's pretty much the stereotypical dream guy, right? How much older is he? If he's so much older that you're going EWW! at the above paragraph, well, why are you hanging out with him in the first place? You should have realized when he offered to pay your tab that he was interested. Old men are generally gentlemen, but that doesn't mean they're any less interested in a pretty girl than young men. Sounds to me like sending you flowers and paying for date after date IS his way of making a move- you're just so used to the "hey, baby"s of this generation that you failed to see it.
controlledspin controlledspin 8 years
My immediate thought was this after I read this - Are you REALLY questioning his true intentions, or do you already know that he has feelings for you, and are just using this 'unknown' as a way to keep accepting his gifts? The best thing would be to make sure that you broach the subject somehow, making sure that you don't hurt his feelings at all.
cubadog cubadog 8 years
I am in a similar situation and you need to make sure that you are up front and let him know that you are not more than friends. It has been my experience that most older men have a tendency to always pick up the check no matter what the siuation it is called being a gentleman. My friend Jake knows and understands that we are not going to be more than friends. When he has a professional dinner to attend, he'll call and ask if I can be arm candy! I thnk it would be nice if you insisted on picking up the check the next time you go to lunch.
vaportrailed vaportrailed 8 years
Well, you can treat it as a platonic relationship. If he decides that he has feelings for you, and you still have none for him then let him down gently. Nobody should do anything at random and expect any sort of "favor" in return that has decency in the first place.
ClassicsDiva ClassicsDiva 8 years
I agree that the best thing to do would be to talk to him about it directly, but, if you're painfully non-confrontational, like myself, the safest thing to do would be to assume he just wants to be friends, and then watch yourself like a hawk to make sure that you don't do anything that might lead him to think otherwise. No flirting, no physical contact, no use of the word "love" and liberal use of the word "friend." He may not be making his intentions clear, but that doesn't mean you can't make yours clear. Of course, if you're really passive-aggressive and have killer penmanship, start writing him thank you notes on fancy stationery for the flowers and the dinners, and sign them "Respectfully, Greta." If that doesn't get your message of "not interested" across, nothing will.
ThePerfectScore ThePerfectScore 8 years
Hmmm I wonder if I should feel bad? The guy I'm dating has showered me with gifts since the very beginning. Our very first date was at the High Art Museum, a major step up from a typical movie. Our 3rd date was at this gourmet restaurants, and being the tacky person I am, I had to see the bill! I was $140 just for dinner! So heck I never offer to pay :) He seems to get off on being "the man"... so I let him have it.
tinywhale tinywhale 8 years
Generally I agree with everyone else before me. This man must be romantically interested in you to take all this trouble. But there could be another explanation: as you say this man is older, so maybe he belongs to another generation where it was considered an absolute must for a gentleman to pay for lunch and to send occasionally flowers. Anyway, I agree with vanyvrgs that you should talk to him so that you can be sure about all this. You will ruin this friendship by doubting his every move if you don't clear this up.
katlovesclothes katlovesclothes 8 years
Here's a gentle suggestion: go out to dinner/lunch/whatever and excuse yourself at some point. Once out of his sight, give your credit card to the server, open a tab (so to speak) and tell him to tell the date that the check is "covered" that will give you some control!
Muirnea Muirnea 8 years
My bf tells me the same thing that clarapl was talking about, that guys don't do things like that just to be friends, where we girls would. I'm guess there could be exceptions of course, but my guy rolls his eyes etc. when I tell him things like that, lol. You should just talk to the guy about it, and be honest when telling him your feelings, you shouldn't feel stupid because he should understand that you can't read his mind! lol. Good luck!!! :-)
clarapl clarapl 8 years
I don't really see how sending you flowers can seem open to interpretation to you..seems he's making his intentions pretty clear! Recently, an older man who struck up a conversation with me in a restaurant tried to insist on picking up the tab for my lunch, and I refused to let him, it just didn't seem appropriate, even though we'd had a nice conversation and he was extremely polite. Later, I worried that I might have offended him or jumped to conclusions, but when I asked my male friends about it, they pretty much rolled their eyes at me that I could even doubt the true nature of his obvious intentions, as gentlemanly as he was... Don't you have any guy friends you could ask? I bet they'd clear this up for you pretty quickly!
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