20-Something Question: Is It Time To Move On?


Q. I’ve been seeing a guy for two months who I like but I don’t know if he wants a long-term relationship or just a fun buddy.


He’s very busy between work, playing a sport, and renovating his house. It’s hard to spend a lot of time with him because I work at night and on the weekends at a bar. I’m also training to become a nurse.He comes to the bar a couple times a week and we connect when I’m done working but we literally fall asleep, wake up, have sex and go home. We hangout sometimes on the weekends too and we enjoy cuddling and relaxing together.


My dilemma is that we are still awkward as far as making plans/ knowing where this is going. Part of me thinks I’m leaving too much in his court. But then another part thinks I’m not giving him enough signals that I like him.


I have tried complementing him, telling him I find him attractive (he told me I didn’t have to lie) and that I like him. But then I introduced him as my friend to someone else. I also sent him a homemade card for Valentine’s Day and made chocolate covered strawberries and I got nothing. I decided to not make it a big deal out of it,. He tried to make it up to me by taking me out to dinner but I told him not to worry about it. I didn’t want something just because I did something. But would have liked to go to dinner [on his own initiative].


So now that I wrote you a novel — what is your advice?  I want to continue seeing this guy I just don’t know if I’m blind or if I should move on.


I have made a point to have a life, keep hanging out with my friends and have seen other people but only because that is the advice I’ve been given. I staying exclusive (sexually) for the guy I like. Thanks for your help I really appreciate it!

A. On this one the 40-somethings are in consensus — you deserve more.  Or at least you need to spend more time communicating. It’s okay to put yourself first more. You talk about how busy he is but you are working double time. Here is the perspective of 40-somethings who have been there and done that.


Dear 20-something,


You like him more than he likes you. It’s a fact. You have two choices, you can amp it up and be honest, tell him you want more or just walk away assuming you know he’s not that I to it. I always go with choice 1 because you never have to guess about how he feels and you might just be surprised to find he’s scared or shy. If he’s not into it you get out early. Guessing and analyzing every word,  reviewing his texts with girlfriends, and second guessing everything you’ve said is an absolute waste if time. Let him know where you stand and go from there. It’s just always the right answer. — 40-something, director, Global Account Director, NYC


Dear 20-something,


It sounds you deserve more. Though this guy may enjoy your company it does not sound, for whatever reasons, like anything serious or that it has long-term potential. If I were you I would move on, or at least see other people. Or just not date anyone right now and focus on yourself, career and friends. It sounds like you are quite busy with nursing school, etc. Looking back as a married person of 45, I wish I had been OK more often in my 20s and 30s with just not dating anyone for a while. – 40-something, travel / hospitality industry, San Francisco


Dear 20-something,


Seems to me this guy has it pretty good.  He hangs out at the bar where you work, has a couple of drinks, goes home with you, and really doesn’t have to make an effort — or even consider how he would want this relationship to go.  You need to find ways to change this dynamic so that he has to make real time for you–or tell him exactly how you feel and what your needs are at this point.  No one is that busy. –  40-something, consultant, NYC


Dear 20-something,


If the two of you are having sex and it would be awkward to have an honest discussion about the status of your relationship then you are not having a “relationship”.  If he would rather work on his house, than talk to you or spend time with you, you are not having a “relationship”. This sounds like the two of you are having a sexual relationship, aka booty call. – 40-something, fashion industry, entrepreneur, Brooklyn, NYC



Dear 20-something,


He is a friend with benefits. Reading between the lines, it sounds like he likes it just they way it is and happy with the status quo.  You need to give yourself a deadline to how much longer you can handle this relationship and if you want more than he can give, either have a conversation about the status of the relationship or start dating other people.  See what happens next when you say you want to date others — if he is fine with that than you have your answer and if he isn’t then discuss how you can take it to the next level. – 40-something, PR Director, Chicago



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