Dating situation: Does this have a chance to become a relationship?

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Hey Guys,

I have a question about a guy I have been seeing.  I am a single, college educated, never been married, financially independent woman.  I do not have any children or any real issues.  I met a guy who was working as a bartender at a local restaurant/bar that my friends and I hang out at times. I did not take him seriously for about 2 year, but I was seeing someone. But I will admit, I was being a bit elitist in thinking he was only a bartender, etc.

Well, over the past 4 years, we have been going back and forth, on and off.  He, at some point, met a girl and she became his girlfriend.  It sounds like she hurt him a lot, and when they broke up from time to time, he would contact me.  I finally started liking him, but we kept getting interrupted by the timing–he would get back with his ex or I would meet someone.  Now since February, 2011, we have been kind of seeing each other.  I asked him if he was over his ex and at least open to seeing what might happen between us. He said yes.  We had not slept together until after this conversation.

He just graduated from art school and I left him alone to finish his final projects. Last Friday, I was out with my girlfriends celebrating some birthdays.  My guy, let’s call him Steve, and I had gotten together on Tuesday and had a great time. We made plans for Sunday, but I kinda wanted to see him Friday night when he got home from work. I kind of pushed it a bit.  I was a bit tipsy, and I got a bit wild.  I guess I said somethings like, “Do you believe people can stay this attracted to each other over time?” and “Steve you need to get tested.” (We had discussed this before because I am very adamant about this and he agreed!.)

We also decided to go on a little trip— my treat for his graduation. So I asked him when he thought it would work for him.  I might have said some other things, but honestly, nothing like, “I want to marry you.” or “I love you.”  So Saturday morning, in my gut, I got this weird feeling he was freaked out.  I went running and thought about it.  I sent him a text saying, “Hey Steve, I was kinda drunk last night and I went running and just got back.  While I ran, I thought about my behavior last night and I am sorry if I was over the top. It was not my intention.”  He did not respond to the text.  Later, around ten at night, I texted him to just say, “Hey,how is work going?”  No reply from Steve.  So now I am really feeling like he is totally wigged out and I was right.  Sunday comes and no call about our plans.  So around noon I get back from the gym and call and say, “Hey are we still on for today?”  He calls back around 3pm to say that he needs to distance himself from me and that I am getting too attached and he doesn’t want to send me mixed signals.  So I call back then hang up and text and say, “I was drunk, that is why I texted you this morning, can we talk?”  He says yes, I will call you later. We had a really good conversation. I listened and he said he didn’t know why he was so freaked. I asked him if he wanted to take some time to be alone because he has had a lot of transitions lately with graduation, getting over the ex, trying to decide about work, etc.  I get that!  He said no he liked me, liked being with me, and didn’t need to take time.  So then our conversation ended and I thought it was resolved.

I didn’t contact him all week and I didn’t hear from him.  Friday afternoon I text him, “Hi, Steve, how are you?”  No reply.  We are friends on Facebook, so I  looked on his page, and he posted at about 11 pm on Friday, “I am heading to the backwoods this weekend on my Harley, etc..”  And I never heard from him.  So I went on with my Memorial Day weekend.  But I am still really hurt and confused by this.  I said to him on Monday night that to me, talk is cheap, and a person reveals his/herself by actions. He agreed.  So now I feel like he is blowing me off—and I really don’t want that to be the case.  I will not call or text him but I don’t know if I will hear from him again.

What is your advice or insight to this situation?  Am I just dreaming to think that this could be any kind of relationship?  I wish I had listened to him on Friday and skipped going over to his house, but I was out and really wanted to see him. I guess I totally screwed this one up.  Thanks for your reply.


Dear Nan,

Thanks for your question.

It is possible for people to move too fast, or move too slowly, or say the wrong thing at the wrong time.  But generally, if that’s all it takes to mess up the possibility of a relationship, we tend to think it was probably not going to happen anyway.

It feels like you’re having to force this relationship on “Steve” and that shouldn’t be the way it is. We still don’t think you’ve done anything we’d consider a “deal breaker.” If he was really into you, or really wanted a relationship, he would welcome your tipsy advances, unless you were way over the top, or completely embarrassing, which doesn’t sound the case. And even if you were, you apologized and tried to make it right, which shows your reflective, self-aware side. In our minds those are great qualities to have.

“Steve” is in a transitional phase of his life as you know. It doesn’t matter that he’s older than some guys in this stage. The fact is everyone’s timeline is different and he’s gotten a late start on his career path. He needs time to figure out where he’s going and what he wants. He also sounds like he’s still torn emotionally over his ex. He needs time to do his thing, on his own terms. And isn’t that the way life is? It’s all about timing. And in your case, it feels like the timing just isn’t there.

So our advice is, let things play out on his terms. He has to be the one who initiates with you, not the other way around, which has been the case up until this point. Let him contact you via texting or calling. Let him ask you out. Let him be the one to plan any weekend getaways. And see how it goes. If nothing happens then you’ll know it’s not the right time for him. As far as having physical relations with him: please be careful. It’s likely if he calls you out of the blue, he’s seeing other women besides you. You’ve got to be safe out there.

We also think you need to put yourself back out on the dating scene when you’re ready. We know you’re still into this guy, but if you can keep a little of yourself open to meeting someone new, this might be a really nice thing for you.

Please leave us a follow up comment, and keep us posted. (Feel free to ask another question anytime.)

Good luck,


ps. Please spread the word and let your friends know about us.



16 Comments on Dating situation: Does this have a chance to become a relationship?

  1. Dear Guys,
    Thank you for your recent answer to my question. I did what you said, and now, “Steve” has been initiating activities with me. We did not speak for several days last week. I had a bad car accident on Monday night, and I did call Steve because I was upset and alone. He was sympathetic, but was not near the accident site. He called later and texted to see how I was. My question is that for the remainder of the week, and in general, my attitude has changed. I did not contact Steve all week, and I waited to see what he would do as I think he should initiate as you said. Saturday night I was out with friends, and Steve texted me asking what I was doing and he ended up meeting us. I went back to his house after, and he and I had a long conversation or I should say he openly spoke to me about how his ex girlfriend and the fact that she had moved in 5 doors down from his current apartment. He stated that he was fearful of seeing her with another man, which he did, and he was okay with it. He expressed to her that he did not want to be around her etc. He stated to me that he was really done with the relationship and that the fear of the unknown was a lot of what was bothering him. So, he asked me out on a date for Sunday, which was to the movies and was nice. He said that he thinks that I should go to a 4th of July party at his boss’s house, etc. and he seems to be into the situation. I still am kind of mistrusting of the situation and I really am not sure what to do. So my feeling is that I should just do nothing and see what occurs. I think that he needs to follow up regarding the 4th of July so I am not planning on going to any party with him–I am making my own plans. I am also planning a trip to Las Vegas right before the 4th and I am really not saying anything to Steve about what I am doing. Do you think that is the way that I should handle the situation? Just let it go and see where it ends up? I don’t feel comfortable about his ex girlfriend being so close by, I think that she has m!
    otives t
    hat are not honest. She does not hold a job and uses men to pay for her bills, rent, etc. I don’t understand why Steve would even want a person like that as a partner, but I realize we cannot change our feelings for someone over night. Should I be worried about her? Also, his sister is coming into town this upcoming weekend, and I am just going to let that one go, too. I am not insecure or clingy by nature, and will not allow myself to act in that manner. However, on Sunday night , Steve made one comment that I was not sure of the time frame of and it is sticking with me. He said that he and one of his guy friends and he ex girlfriend went out Monday night and were hitching a ride to go out–my thinking is…I called you that night after I was in a car accident…and you are out with your ex? But I am not sure if this is a current incident (meaning happening on that date) or an “old” incident…but in my gut I feel weird…I want to ask him, but my pride is saying just let it go. Should I ask him about it in a non-judgmental manner to get clarity? Or just let it go and see what happens? I am making a donation to your site. Thank you so much. Nan

  2. THE GUYS // June 20, 2011 at 3:01 pm //

    @Nan…’re taking the right approach. In this situation you have to see how it plays out. You’ve already done most of the initiating. And even if he’s not with his ex, she’s close by, and they still have some sort of emotional bond—hopefully nothing more. So until that’s resolved, and until he starts really stepping up to the plate, you don’t owe him anything.
    Have fun. Do your own thing. And see what happens. Hopefully it will all work out. But it could take some time.

  3. I tried to find a question that was related to mine, but I had some trouble posting a comment, so here goes…I am 39, with two kids. I haven’t dated in 9 years because my last boyfriend was physically and emotionally violent, and it took me a long time to clear my head. About 4 years ago, I met a man through my job. I see him frequently, and have often wondered if he was interested in me (other people have mentioned that they thought he is, although they are basing this on his body language, not anything he’s said.) He’s 45, was divorced several years ago (and from what he’s said, which is not much, it was a brief, unhappy marriage), and shy. I used to just say hello to him, and he’d blush (he blushes with almost everyone, though, not just me), but now we talk more, and he doesn’t blush as much. I know that before, I wasn’t interested in him because I didn’t want a relationship with any man. Now, I make reasons to chat with him, and he seems to be responding. He just seems to be very kind and gentle, and everything I’m learning about him is good, so far. (No red flags.) I want to ask him for coffee (and more) but I am terrified. I am still a bit insecure, as I’m overweight and look nothing like models/actresses, etc…, and I’d like to feel a bit more on solid ground as to how he feels. We don’t work together, exactly, but I’d still have to see him frequently at work, and I know if he is not interested, he’d be kind about it, which would be worse than an outright rejection. I’ve thought about this for 3 months, and I can’t seem to make that step. Any advice you have would be wonderful.

  4. @Sara…..We understand your reservation, especially since he’s someone you would see frequently if it didn’t work out. Ideally he would make the first move and ask you out. Then at least you’d know if he were interested in more than just a friendship. If you ask him out for coffee it will be ambiguous. He’ll wonder: Is she asking me out because she enjoys my company? Is she interested in me? Is this work related? What’s going on? Also, if he’s kind and shy, he might say yes for a variety of reasons. He might be genuinely interested or he might say yes just to be nice. So the best thing to do is keep talking with him. Try to get to know him and maybe drop a few hints about some things you like to do, or even, that you’re single, etc. Try to be casual and funny; even a self-deprecating tone works well. See if he bites. If he doesn’t you might need to take the leap and see what happens. At least you’ll start getting some answers. But for now, be patient, and give it a little more time. Good luck. Feel free to leave us a follow up comment/question. And keep us posted. We hope it works out.

  5. The difficult part is that when I do see him, it’s in my small office with 6 other people around, and it’s usually pretty busy. I also know that he’s very busy, works late, etc. Sometimes he only stops for a moment, but the other day, when only one or two other people were around, he stood and chatted with me for several minutes. When I said, “Sorry, I know you’re busy and don’t have much time to chit-chat” he said, “oh, no, it’s a nice change.” It’s just hard to gage things with so many people around, but I was rethinking this myself and I guess I’ll just try to be patient. Thanks for the help! I do appreciate it.

  6. @Sara…..Good luck. You’ll know when it’s time to make your move. And hopefully he’ll step up to the plate first! Take care.

  7. Glad I checked with you guys first. Not sure why, but he’s suddenly become very cold and indifferent to me, and was kind of rude yesterday, actually. Guess he’s not interested. Glad I didn’t make a fool out of myself first.

  8. ey guys I don’t know if you remember me but I asked a question last time about a guy and you guys said the answer was he was leasing me on just so he can get what he wants and that was it and that we prob wouldn’t date and that I was holding on for no reason, and that I should move on, well he did tell me sorry for leading me on and that he was going to hurt me but that I was amazing he just isn’t ready for a relationship yet and he isn’t the man he wants to be yet, he said yes it’s possible to be together in the future, but right now he isn’t ready, he says every time he likes me he always likes another person to. He knows my feelings are strong for him over the almost 3years of knowing him and this kind of relationship since November. I just wanted to ask you guys, what should I do now?

  9. Hey guys I don’t know if you remember me but I asked a question last time about a guy and you guys said the answer was he was leading me on just so he can get what he wants and that was it and that we prob wouldn’t date and that I was holding on for no reason, and that I should move on, well he did tell me sorry for leading me on and that he was going to hurt me but that I was amazing he just isn’t ready for a relationship yet and he isn’t the man he wants to be yet, he said yes it’s possible to be together in the future, but right now he isn’t ready, he says every time he likes me he always likes another person to. He knows my feelings are strong for him over the almost 3years of knowing him and this kind of relationship since November. I just wanted to ask you guys, what should I do now?

  10. Hi! I just want your opinion on my situation. I met this guy from work and been seeing each other since. I already had a feeling that I was becoming a booty call but disregarded the feeling. Then I found out that he was dating this girl since June (We’ve been seeing each other since Feb 2012).

    I decided to stop seeing him for a while, but I still gave in. He said that the girl was not serious and they are not together together. But I saw their facebook accounts which totally say a different thing.

    I want to forget about him, but I fell hard for him. I am not ok with him seeing another one and I know, I am totally the other girl in the picture. What really messed me up is one time, he came over to my house and started to talk. He was asking questions like, “what if we were a couple”

    What should I do?

  11. @Emmi…..Thanks for your donation. We appreciate it. We hate to say it but we don’t see a future with this guy. He’s a player. He was dating two girls at the same time, and not being open and honest about it. We know you really are into this guy but you’re settling to be with him. You deserve much better than this. Our advice: Move on. Find a guy who will treat you with respect; and love you the way you love him.

  12. @Anna……Nice to hear from you again. We still don’t see this going anywhere unfortunately. These are all excuses. And don’t you find it interesting that he always like someone else at the same time he likes you. Seems like a player to us. We’d suggest moving on. Sorry. Good luck.

  13. Dear Guys,

    I met this guy on a online dating site. We texted each other for about a month before deciding to meet. This guy knew already that at 23 I had not had my first kiss and that I was a virgin. So on our first meeting we held hands and ending up kissing and I went home with a hickey on my breast. I was very giddy about the turn of events and did not feel weird about how fast things moved. On the second date things got hot and heavy and we got to 3rd base. I was the one that initiated the events. Again I did not feel nervous or scared to be doing these new things I was completely comfortable with this guy. So far we’ve been out 6 times, he has casually met my mother and he invited me out with his friends. So the problem is that since oral sex was done early on I feel that he expects it to be done every time we hang out. He is a great guy. He’s kind, chivalrous and makes me smile. But I feel like there is an expectation now. We’ve barely been dating for a month but things have moved pretty fast. I told him that when it comes to sex I will not have it until we are A: in a relationship and B: there is some sort of feeling other then lust. I felt that he understood my wishes up until a few days ago. (He is a virgin as well) He told me he wants to have sex already and that he doesn’t want to be a virgin anymore. I told him that I understand how he feels and that if he cant wait for me to be ready then he can obviously go out with another girl who isn’t waiting. He said this whole conversation made him feel awkward since we have conflicting feelings. So my first problem is what do I do about our conflicting views on sex? Why isn’t he committing to a relationship when he hints at the possibility and after I told him if he asked me I would say yes? And lastly when I’m with him I’m happy and every things great but when I get home I feel like it is all not as great as I thought? Is this normal for me to feel when we are apart? I’m thinking it might be an omen but I have no idea since I’ve never been in a relationship or with a guy. I’m sorry for the jumbled mess but I have no idea where to start or how to ask. Everything is so overwhelming. Thank you so much. Completely confused.

  14. @Jen……We can understand why you’re confused and possibly a bit angry about his lack of initiative. But you can’t lash out at him and then tell him to go after another girl. You’re just going to push him away. We agree he needs to make up his mind soon about what he wants. And we agree if he’s not going to commit to a relationship with you then he shouldn’t be expecting sex, whether it’s oral or intercourse. How old is he? And how long have you been dating?

  15. Thank you for the response Guys. The fellow and I are both 23 years old and we have been dating for 2 months going on 3 but for me it feels like since things have been moving fast in those 2 months then there should be more recognition of a relationship possibly happening. I think I just need to give it time. I’ve had a few days to ponder on our sex conversation. I’m hoping he turns out to be the type of guy that is okay with waiting and won’t continue to put pressure on me to reconsider my opinion on sex before a bf/gf commitment. But I guess only time will tell. Thanks for the feedback it is nice to hear another persons point of view on the situation!

  16. @Jen…..You’re welcome. Good luck. We still think you should cool it a bit on any of the sex—third base, etc—until you have a relationship conversation.

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