How Do I Get A Guy to Make A Move After I Rejected Him Once?

How Do I Get A Guy to Make A Move After I Rejected Him Once?

Hey Evan,

Your advice is great and seems to pertain to guys you’re already dating. I’m in a different situation. I’m interested in dating a male friend.

We met in college but were never really close and reconnected a year ago purely as friends. We started hanging out a lot the past year. He used to live two hours away so he would drive from far away to see me. I thought nothing of it. Then he moved to my city and we were close to each other now. One night we went out and he made a move on me. I froze. This was three months ago. We kept hanging out then, pretending nothing had happened, me sending mixed signals, both of us casually dating other people.

But I recently broke off casual dating because I realized I had strong feelings for him but now I wonder if it is too late? I still spend a lot of time with him and I don’t want to emasculate him by not letting him make the first move. We recently got back to a great momentum where it isn’t weird after all the mixed signals and I feel like I am ready to tell him I wasn’t rejecting him when he initially made a move on me but was just scared and surprised.

So should I make a move or will that emasculate him? And if we do date, do the same rules apply? Should I wait to sleep with him? Because I feel like we already have been on 100 dates (platonically), I don’t feel weird about sleeping with him sooner than I would wait for a guy I really like.

Help please.

If you want to know what a man’s thinking, ASK HIM. Don’t ask your friends, don’t ask your dating coach, ask your boyfriend.

Dear Jeannie,

I was hoping someone would ask this question.

Because it gives me a chance to bring something up that I see all the time as a dating coach, especially in my private member forum. In that group, hundreds of women share their dating stories and support each other. And most of their questions sound just like what you wrote to me.

“I don’t know what this guy is thinking. I don’t know what to do. I don’t know what to say. What do you guys think I should say?”

This happens so often that I created an acronym to substitute for my full answer, so that I don’t have to write the same thing repeatedly.


It stands for “overthinking”. Almost any time I get a “what is he thinking?” query, I’ll bust out my OT as a reminder of two of these two core dating principles:

1) Men do what they want. So if a guy is your boyfriend, he says he loves you, he calls you nearly every day, and then one time, he texts you, “Not now. I don’t feel like talking,” it doesn’t mean that he suddenly fell out of love with you, met someone else, and is planning on dumping you the next time you speak. It just means, “Not now. I don’t feel like talking.”

2) If you want to know what a man’s thinking, ASK HIM. Don’t ask your friends, don’t ask your dating coach; ask your boyfriend.

The reason that women choose not to ask their boyfriends what they’re thinking, even though their boyfriends are actually the only people who KNOW what they’re thinking?

The act of asking the question isn’t going to change the outcome — all it’s going to do is reveal what he’s thinking.

Well, there are two answers to that as well — the one you tell yourself and the one that’s really true.

The one you tell yourself is this: “I don’t want to upset him/emasculate him/bother him.” There’s some basis in truth for this, especially if you are perpetually acting weak, needy and fearful with a man who is doing his best to please you. The more you criticize and second-guess the intentions of a GOOD boyfriend, the more likely he is to get frustrated that you’re so insecure.

But the real reason you don’t ask him what he thinks is this: you don’t want to hear the real answer. You’re afraid of the truth. That he might be sick of your fears and insecurities. That he might need space. That he might be tired of the incessant conversations about where this is going, because he doesn’t know where this is going.

As always, I’ve hijacked the original question to make a point, and I apologize. But it’s important to know that your question is NOT going to change his mind on anything. His mind is already made up. If he’s happy with you, he’s happy with you. If he’s annoyed with you, he’s annoyed with you. And if he’s attracted to you, Jeannie, he’s attracted to you. The act of asking the question isn’t going to change the outcome — all it’s going to do is reveal what he’s thinking.

The only thing up in the air is whether you really want to know.

So instead of asking a dating coach on a blog who doesn’t know you or your friend what he’s thinking, how about you tell him EXACTLY what you told me? You were afraid when he made his move, now you’re falling for him, and you’d like to give things a shot.

If he’s not interested, he’ll let you know.

If he’s interested, he’ll let you know.

And either way, you’ll be able to move forward appropriately without all of this worrying and overthinking.

(By the way, he’s interested. I’m very happy for you!)

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  1. 21

    Wrong wrong wrong. Touch him when you talk to him, smile lots, show interest in what he is    interest in what he is saying and listen lots. Men do not give up if they want you. You just need to give lots of positive reinforcements so that he knows, when he does make a move, that you won’t reject him….

    1. 21.1

      sorry elle, at this point she has to make the move, we only try once, we don’t want to be creepers. “positive reinforcements” the same reinforcements that thought it was ok to ask the first time, you are wrong here because he is probably in a state of confusion if not a little bitter so he won’t let his guard down in other words “i did it and I’m not making that dumb mistake again” at this time she has to have a conversation with him explaining why she did what she did and why she changed her mind and why she now thinks he is the guy for her now but not then. Pretty much somewhat of an apology for rejecting him for whatever stupid reason she had (most likely based on things like looks, height, etc) and then she can only hope he accepts her move

      1. 21.1.1

        i meant that he had though not that thought

  2. 22

    Women don’t ask the guy and instead ask her friends because we think the guy can be a jerk who is well back him up to keep the options open 🙂

  3. 23

    It seems like us women tend to be over thinkers. I hate it and want to change it. The question is how? The guy I have been seeing for almost a year is amazing and yet I will over think everything.   I tend to blame it on my past relationship but I know that is not his fault! But if I don’t get to see him as often then my brain starts going and that will be what kills our relationship before anything else.   And even knowing that I struggle!   Reading that others deal with the same issues is helpful, especially when they give ideas on how they were able to control it more.   It’s also helpful to hear the male side of things. Since we think so differently it helps to have that insight. Thank you EMK for this forum you have given us!

    1. 23.1
      Karl R


      There’s a simple rule of thumb that I learned from another dating expert.   (Evan doesn’t have a monopoly on good ideas.)

      With any relationship, do a three month progress report.   Before the end of the first three months, you should be boyfriend/girlfriend.   If not, you never will be.

      At the 6 month mark, your relationship should have made noticeable progress forward from where it was at the 3 month mark.   At the 9 month mark, your relationship should have made noticeable progress from where it was at the 6 month mark.   And so on.

      If your relationship has stagnated for three months, you can address the topic of “what do you want out of this relationship” or “where do you want this relationship to go” with your partner.   It’s likely that the relationship has stopped moving forward because one partner really doesn’t want it to go any further.


      There’s a natural ebb and flow to relationships.   There won’t be consistent growth from day to day, or week to week, or even month to month.   That’s perfectly normal.

      By looking at a 3 month time frame, you can stop trying to analyze the week to week changes in your relationship.   You may end up over-thinking anyway, but it lets you know when you should avoid mentioning or acting on that over-thinking.

      1. 23.1.1

        Thank you Karl! I will try to keep this in mind. I find that if I get something in my head I have a hard time letting it go without saying anything.   I have tried and he always picks up on the fact that something is bothering me.   I obviously read like an open book! In this instance I don’t want to say anything until I see what happens over the next few weeks. The reason for that is that I don’t want to make him feel bad if I’m just bring old baggage in and it has nothing to do with his feelings.   Does that make sense at all?

        1. Karl R

          Karla said:

          “I find that if I get something in my head I have a hard time letting it go without saying anything.   I have tried and he always picks up on the fact that something is bothering me.   I obviously read like an open book! In this instance I don’t want to say anything until I see what happens over the next few weeks.”

          Here’s another trick that may help with that piece.

          This advice was originally given to people who felt something was wrong, and they wanted to snoop on their partner (which is always a bad idea).   With minimal changes, it should work for you.

          Why did you get something in your head?   Generally this is triggered by something he said, did, didn’t do, or by something you observed.   Whenever someone starts over-thinking or over-analyzing (or getting suspicious), it’s based on something concrete.

          Instead of talking about the enormous thing that you’ve created in your head through over-analysis, talk to him about the actual concrete piece that is real.


          For example, I had a girlfriend that only responded to 2/3 of my emails and voice mails, and rarely responded to them in a timely fashion.   (She wasn’t in the habit of checking her voice mail or email more than once or twice a week, and that habit persisted.)

          Internally, it was easy to conclude that she just wasn’t that into me.   However, I always found it more effective to address issues in the most low-key manner possible.

          Therefore, when addressing the issue with her, I believe I pointed out that it was rather inconvenient to me.   I would usually contact her on Monday with an idea for a date on Friday or Saturday.   But given the infrequency of responses, I typically wouldn’t know on Thursday whether she was available or interested in that activity.


          The observation that I made (you’re slow to respond and it’s inconvenient) didn’t try to interpret anything more that I could  observe.   It took  the emotion out of the observation.   But it still addressed the issue.

          More importantly (for you), this kind of observation  also provides an explanation of what’s bothering you.


  4. 24

    Karl thanks again!

    So my issue is that the last four weeks he has only had time to see me on Saturday into Sunday which I realize shouldn’t be a problem. He was traveling one week and he had his kids the other three weeks since his ex was traveling. There was a night twice in the last two weeks that he could have made the time to at least meet for a quick beer (well in my opinion there was time) but he said I want to go work out and get ready for the girls.

    Now our time together is great. I have no complaints so part of me knows I need to just move forward and stop thinking so much. But now I have put other issues into my head and I hate what I am doing!   Part of me feels like I need to talk it thru with him so it doesn’t become any bigger so do I start out by saying…..I know you have been busy the last four weeks and I so enjoy our time together I just want to make sure there is nothing else going on?

    i so appreciate you helping me with this. Just helping some stranger that is very kind!!

  5. 25

    Just a comment from random guy for girls who may be in similar situation. No offence but what kind of nonsence this is?

    ”  I still spend a lot of time with him and I don’t want to emasculate him by not letting him make the first move.  ”


    Really does it make a difference who makes a first move? It seems to be more important for this girl that the guy. Besides he made a first move just the girl skipped it. Well at leat I dont care if girl would say she likes me… Of course she doesnt have to but may send some clear signals that she wants me to be around. Well.. my last attempt ended with girl shouting on me that I am bugging/annoying her. (Difficult to translate to english equivalent). Well I got a hint or actually I should say a warning. Felt  really sad and stupid that I didnt saw it comming and needlessly annoyed her. I think later on I overheard her complaining to her best friend (girl) why some guy  dont invite her anywhere. Judging by other  comments I think that was about me, but after such harsh previous scene I’m not taking chances. Besides there were other signs that normally I would think that girl is interested but on the other hand she  not even acting friendly…

    So it just may be that a guy is still interested but he is sure you will not feel the same and all smal signs are just rejected as his “mind playing trics”. Remmember noone likes being that guy who doesn’t get it. The problem is… We sometimes actually   and don’t.

  6. 26

    Miscommunication between two sensitive people, I really hope it all worked out either way.

  7. 27
    Will S

    “and I don’t want to emasculate him by not letting him make the first move.”

    What century are you living in?

    A) I’d love it if the woman would make the first move

    B) He already made the first move – your turn.
    Why should the man be the only one directly taking the chance of being rejected or screwing things up?


  8. 28

    You rejected him. That means it’s your move. The most emasculating thing would be for him to make a move on you after you rejected him. Depending how you approach it would then be up to him if he gives you a chance to prove you’re not unreliable and just change your mind about things or that you aren’t just wanting him because you ran out of other better options that didn’t present. Even if he is interested (which he is by the way otherwise he wouldn’t spend time with you), believe me if he is a man of integrity you are going to have to work very hard for this and so you should.

  9. 29

    It’s very simple, she didn’t find him sexually attractive before and now she does. This is a common mistake women make. Rejection is horrible for “nice guys.” She clearly put him in nice guy territory until she realised he is much more than what early impressions gave. The only way things are going to happen is if she makes her intentions clear. The thought that he could get rejected again will assure her that she needs to work her butt off to get him, even if he is interested. If he is a real man he will make her do the work.

  10. 30
    Eric Souza

    How Do I Get A Guy to Make A Move After I Rejected Him Once?

    Really? How do you get to make a guy move after you have rejected him? This is not fair. The girl should make the move and try to approach the guy after rejecting him.

  11. 31

    Nice reading all of the comments! Nice to agree to disagree, we can all agree love is what we believe it is. When we love ourselves we are open to be free and do what our first mind tells us. 2nd guessing is why we question ourselves. I say go for it! If your heart says you are ready I do not think you have to explain why you did or did not. Being present in the now makes us real people and not critical. I agree with Eric btw who keeps repeating himself because we need to listen to his point. We live and learn and regardless of the outcome we can say we went for it and all is fare in love and war. Follow your heart and I think you will be glad you did…but be aware not apologetic. Good luck and ttyl.

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