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. 1

    Ahhh the ‘OT.’   I have that problem all the time and am really trying to curb it more now that I’m in a relationship with a great guy.     He always tells me how happy he is, how he loves doing things with me, and even decides to go to places with me instead of his buddies, but my mind still manages to question what’s going on at random times.     ‘He didn’t say he loved me today, why not?,’   ‘He wasn’t as happy/chipper this morning leaving for work, did I do something wrong?,’   ‘He says he loves the amount of time we spend together, but does he really or is that what he thinks I want to hear?’ OY!   The OT can be the worst thing to your relationship, or in this case to your almost relationship.     What I’m coming to learn (and forcing myself to learn) is that I cannot change him, how he acts, or how he feels, I can only listen to what he says, see how he acts, and if things go south, they do, but worrying about that now will only hinder all the good we have now.     Be secure in who you are and who you are in your relationship, the insecurities (and sometimes repeated insecurieties) can only damage your relationship.    If you’ve asked it once, that’s the correct answer, if you ask it again, it’s annoying.  

  2. 2

    Aw Evan, this one was great and actually found it very funny. Good luck to the writer. 🙂

  3. 3
    Jackie Holness

    Yes, if he weren’t still interested, he would have stopped hanging out:) Men are simple. Only women are complicated…No offense to men…:)

    1. 3.1

      You think we are simple, trust me you being a woman, you do not know how complicated our emotions can be. I have continued to hang out with women that rejected me because eventually i just saw us as friends. A couple times, just like the op, they started to like me and I ended up rejecting them cause now I was the one that just wanted to be “friends”, let’s just say they did not take it as well as I did, but I do not understand how a woman like this is gonna think that if they reject a guy and eventually start falling for them, that all is clear. Ladies, when you put a guy in the friend zone, they will eventually lose all attraction they had for you, we start seeing you as like a sister and at that point we lose all sexual attraction. It is kinda naive for this woman to think that she can reject a guy and then all of a sudden fall in love with him and he accepts that she “made a mistake” or “knows better now” or he lost weight and is now attractive and her and this “nice guy” will end up having passionate romance. Sorry Ladies, it doesn’t work like that. again, we are complicated too

      1. 3.1.1

        So you’re saying that if I rejected a guy a year ago, because I wasn’t allowed to date, and we don’t ever talk anymore, I have zero chance of ever having that relationship again? O.O

    2. 3.2

      Jackie Holness said: “Men are simple. Only women are complicated“.

      Close, but not exactly right, the correct version is:

      Men are simple.   Women complicate everything.

    3. 3.3

      Men are   LOGICAL,women are complicated.No offense   to women.

      1. 3.3.1

        most humans are less rational than animals,…

        the only rational humans are mathematicians and scientists (a great number of them women)

  4. 4

    Great Great post Evan.
    Yes Jackie Holmes. Spot on. Most men (not cads or players) are simple in that they :
    1) mean what they say
    2) don’t do what they don’t want to do
    3) only remember things said to them or done to them if they are really really important to them
    4) only requirement of women is that the women like them and are pleasant to be around – no long laundry list of expectations she has to meet
    5) don’t fret over every single thing that their women do or don’t do.
    Women overanalyse men because they think men are just as complicated as they are.
    Yes, the “friend” would not be hanging around if he wasn’t interested at some level. Men don’t waste their time like this if he is in the market dating. If he was insulted about being rejected or took offence in any way, he would’ve been long gone. And since they are already friends, I doubt he would be put off if she was upfront and honest with him about their romantic future. This is not some first date kind of thing while people are still sussing each other out.

    1. 4.1

      sometimes true, but not all the time
      1) sometimes we do give off mixed signals, especially if we don’t want to hurt anyone’s feelings, at this point we will say something and not mean it.
      2) sometimes we end up doing things we don’t want to do (shopping with our girlfriends, visiting our grandparents at the nursing home, etc)
      3)I have a great memory and can pretty much remember most things said to me and done to me.
      4) lol, the whole men will blank anything that moves argument, lol. Some men may be like that. But some men may have list of requirements they expect in a woman
      5) well this one may be true

      again, i love it how these women can make assumptions and say us men are all simple, they all think this way, blah blah blah. You are not men, so you do not have a clue what goes on in our heads just as much as we do not have a clue on what goes on in yours.

      1. 4.1.1

        a great probability is that there is not much difference about “what goes on in your heads or their heads”, we just play different roles (female-male)

  5. 5

    I kept thinking about one thing as I was reading Jeannie’s email:

    “A man will not consistently hang out with a woman once or twice a week unless he likes her.”

  6. 6

    She froze up(or rejected) the first time and now she doesn’t want to emasculate him?   She should fix her own “changes of the heart” either by asking or making.   How does someone in their right mind expect or hope someone will make a move twice?     Maybe the man doesn’t want to be a pig.

    1. 6.1

      she did not have a change of heart, she ‘froze’, she did not expect that, she was confused

  7. 7

    Ahhhh…that was such a cool tagline, Evan!

  8. 8

    Good answer. Since the man already made his move, there is nothing “emasculating” about bringing this up again. The fact that he sticks around is certainly encouraging. If he’d had a change of heart, he’d probably be seeing other women by now. Guys these days seem to be conditioned to not be “creepy” by being too persistent. If he got one no, and still wants to be around you, he probably doesn’t want to risk becoming a pain you want to get rid of.

  9. 9

    Do we get a follow up posting after she talks to him? I don’t know about the rest of you, but I want to hear how it ends up!

    1. 9.1

      if she acts quickly maybe it may end up being ok, if she waits it out, she would eventually be considered like a sister to him and it will not end up well at all. But then again if she does this too quickly there may still be some bitter feelings and he could flat out reject her in anger. So not too soon not too late

  10. 10

    Funny I think when it is right, there is no OT at all. They call when they say, do what they say, and see us every week. The OT is when it is not right and we are thinking of 100 reasons why he didn’t do the above.

  11. 11

    Who are these men that have time to “hang out” platonically with women that aren’t attracted to them, how old are they,  and why would they? I know for myself at 51 being a very busy man I don’t even think about doing such a thing. I don’t have the time. Why? Because I have “options” and I let women that I don’t have time for that sort of non sense. The  one woman that tried that  “friend zone” drivel on me earlier  this year learned this because I was honest and told her “I’m not on Match looking for a hang out buddy, we’re either going to date like adults or this will be goodbye and you can call me IF you change your mind” and she understood. God bless the people that have time in their lives for platonic adult friendships. This guy put in what sounds like a lot of time (pining and fawning over)and it might according to the OP come  to fruition but it sounds like a lot of trouble for a”maybe”.

  12. 12

    @JB, you sound very goal oriented.   In the years before I met my fiance, I did the platonic thing with an ex-gf because the friendship was one I valued.   It was about being the now and the moment. That time together enriched my life immensely for quite a while after our relationship ended.   Yes, there was some tension there and as a result I wasn’t as lighthearted as I normally am, but my friend and I agree it was worth the time spent.   I did harbor a glimmer of hope from time to time, but that was not my motivation.   It was all about being with someone I cared about and enjoyed a great deal. Did it mean less dating and putting off meeting my fiance?   Sure, but it was worth it.

  13. 13

    The growing emanicapation of women has many benefits besides those dealing with increased sexual freedom and improving economic freedom and power:   Women are now increasingly exposed to the fears resulting from rejection that men – previously the hunters – have always been exposed to.   I posit this will help men and women to better navigate the sometimes difficult terrrains of courtship because we now share some of the same insecurities we ostensibly both have and understand each other better given common experiences.

  14. 14

    This is the old Tom — my identity has been usurped!

    I agree with Jackie Holness, Leo and JB — men rarely put too much time or effort into platonic relationships if they don’t have  some hope of more (although it does happen). The fact he’s still there is a good sign. The fact he already made the first move should reduce the risk of him “feeling emasculated” if the OP makes a move.

    In this situation I don’t think the same rules apply Jeannie, so sleep with him as soon as you are comfortable, i.e. now 🙂

    1. 14.1

      I would disagree, ive eventually kept on hanging out with female friends cause I eventually only saw them as friends, in a couple of cases they started to have feelings for me when i didn’t anymore and i rejected them. So I would say, if she does it at the right time, maybe he will be interested. If she waits too long though, she risks being in a position where she is like a sister to him ( now she is the one that will experience the heartache of being in a Platonic relationship since he is no longer attracted to her) if she does it too quickly, she may do it at a time where he might have some bitter feelings from being rejected and would end up angering him which would result in rejection for her. I would say the right time and place in this situation.

  15. 15

    I agree that this girl will have to “make the move” now as he’s hardly going to try again after her previous reaction, but I think she needs to give some thought as to the “move” she makes. Much as men like sex, I think if she made a move on him sexually, out of the blue, as it were, then this might confuse him – he might wonder if she just wanted to hook up for the night with someone she felt was “safe”. A conversation would be better, but I’m also wondering about a letter. Not a text or e-mail, but a good old fashioned letter. Its sweet, it allows her to choose her words carefully and it also allows him time to digest what she’s saying without having to respond immediately. Also, if she ends it with something like: ” I don’t know if you are still interested but if you are, give me a call….” then immediately this puts him back in the driving seat of the relationship. Rather than ” making a move” she’s kinda saying “If you want to make a move again, I’d like that…”

    Just my 2 cents…

    1. 15.1

      yes all could be fine, or he could still have some bad feelings from the rejection and now feel that she is playing with his emotions and will ignore the letter out of heat of the moment anger. I think it would be best for her to wait a little bit, not too long cause he will lose attraction for her (then she is the one have platonic feelings). right time and place in this situation; and I think when she does it, she will probably have to make the move. BTW Ladies, if you make the move, we do not feel emasculated, we might think it a little weird but I think we would accept if we really liked you, if not then hey, now you know what rejection feels like right

  16. 16

    @ JB: you don’t have women friends who you hang out with?   When you’re not actively dating, do you limit yourself to hanging out only with men friends?

  17. 17

    Joe, as JB is in the market looking for a relationship, he is not going to “waste time” on women who are interested in having one with him. Opportunity cost you see – the more time he spends with a woman not interested in him as a romantic partner is time he could have spent with a woman who does.  
    That doesn’t mean that JB does not have female friends or is totally incapable of having female friends. The difference is that he is not likely to spend the kind of time and money on these female friends (who probably don’t expect him to anyway) to the same level as he would spend on a potential romantic partner.   If these women are expecting JB to do this while they “decide” or stay in a holding pattern while they see if the friendship can progress, then JB is being used to some level.
    More likely these women have no interest in pursuing anything with Joe and are only bringing this “friends” business as a polite way of saying “I am not interested, goodbye”. Men generally are more blunt and honest. Joe might’ve picked up on this vibe and wisely moved on.

  18. 18

    Androgynous  is 100% correct Joe. The answer is NO I don’t have platonic women that I “hang out” with. I honestly barely have time for work and  women I’m actually dating or persuing online for “meet & greets”….lol

    I do have female friends that I occasionally “run across” at a bar or singles event that I’ve known for years and I’ll happily chat with them for a bit then move on to meeting SINGLE women I may be interested in. I used to have a couple of women that I just played tennis with (which was great for me because I love to play) but I had NO sexual interest in either and I assume they finally figured out over time that’s  REALLY all I wanted and they lost interest. Oh well.

  19. 19

    she can manipulate him to ask her out….

  20. 20

    I have a strong  suspicion  you are writing because you are drawn to him now he is distancing himself from your rejection (as much as you want to pretend otherwise, from his POV he sure as hell treats it as such)
    I surmise what you’re really asking is “how do I get him to stick his neck out again and ask you again so you don’t have don’t have to and retain the prerogative to LJBF him yet again if I so choose”.  
    If Evan has a trick up his sleeve that I don’t know about how to pull this off, I take my hat off to him.
    But I think deep down you know what you have to do if you want him in your life. And no, the standard ‘rules’ no longer apply. If your parents’ day, yes the males paid for the dates, but the females were equally obliged by social expectation to let the suitor down gently if you weren’t interested and not lead a suitor on. These days are long gone, of course, and I bet he’s already read heaps on the internet about why you dumped him etc. There is a chance that he’ll pretend this rejection never happened but in all likelihood there’s going to be a whole lot of ‘making up’ you’re going need to do to mend the relationship.
    No he won’t feel emasculated if you are suitably contrite about how you rejected him and how much you regret it now. Hey what do you have to lose: if he accepts then you have a shot at lasting happiness and if not, then its a good lesson learnt about letting suitors down gently.

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