He’s Shy, How Do I Get Him to Make A Move?

Question: I met a guy I’m very attracted to; 38, divorced with no kids. I’m 40 divorced with one son. He and my brother-in- law co-own an investment firm. One day my brother-in-law jokingly suggested that he take me out. We had a blast. The next time he asked me out on his own and on the second date, if I may call it that, he said he’d never had so much fun with a woman before.

We’ve been out five times but I’m beginning to think he just wants to have fun hanging out with me and nothing more. It’s crossed my mind may be he is doing all this for my brother-in-law. He compliments me but no sign that says he is attracted to me. He walks me to my door but never tries to kiss me or show signs that he wants to. I just wish he’d take the bull by the horns and kiss me already. Is he shy or is he just hanging out with me because it’s fun?

Yangki’s Answer: It’s hard to tell. On one hand he may just want to hang around with you as a friend and nothing more. On the other hand, he may actually be attracted to you but too shy to express it or afraid to risk that budding friendship by kissing you. The other possibility is that he is just a decent guy who will not touch a woman in a certain way without clear signals from her that she wants him to.

Five dates (yes, I call them dates), I think it’s a great time for you to make a subtle move now. The keyword here is “subtle”.

Shy guys are more of listeners than talkers, so it’s up to you to do most of the talking. Ask him questions about himself — his dreams, his likes, his fears, what his day is like etc. Throw in some hints there that make it obvious to him that you’re interested in getting to know him in a “more than hanging out” friend way. Find out what he is really good at and prides himself in — computers, fixing plumbing, teaching piano lessons to kids, etc and ask for his help. Men and women (but especially men) become more confident and more expressive when they’re doing something that brings out the best in them.

The other thing you can do is next time he invites you out, suggest some fun outdoor activity where you can get closer to each other physically and playfully touch each other. Help him get used to “touching” you without fearing that he might be “misunderstood” … who knows you may might get the opportunity to get that long awaited kiss.

There’s a pretty high chance that you can start something with him that is more than just hanging out or a friendship. Even if he’s not interested in you like that, that’s just life. Okay, things may get a little awkward for a while but life goes on.

Don’t let it go by without you!!!

More from Love Doctor Yangki Akiteng
Disengagement Harmful To Relationships
Disengagement in relationships can be harmful says researcher Keith Sanford, Ph.D., associate...
Read More
Join the Conversation


    1. Some truth there.

      1) If a woman comes on too aggressively because she’s desperate, he’ll sure run. 2) If a guy is not really interested in a woman and just wants to have fun/get laid he’ll get scared. In my opinion, good for the woman!

      But if he is already interested and has feelings for her, he won’t suddenly stop having those feelings because she showed that she’s interested. It actually makes him more interested. For things to “develop naturally” there has to be some positive feedback… 🙂

  1. AvatarAvatarAvatarsays: Frederic

    Bonjour, Yangki

    I was married for 11 years and recently divorced. I’m a bit rusty on the dating scene and come off as shy. Your advice to the women to send some positive signals just enough to give us guys the go ahead is excellent advice.

  2. AvatarAvatarAvatarsays: Musathegentlesoul

    As-Salaam-Alaykum, I come in peace 🙂

    Interesting discussion… I’m 34, shy guy. When I’m attracted to a woman I become shy and always end up becoming her friend. The more attracted I’m to her the more difficult it is for me to tell how I feel. My current girlfriend made the first move and I’m so glad she did. Many women pass up on great shy men because of some old fashioned concept that says women should never make the first move.

    Keep on helping men and women understand each other and relate better. Our world needs more love now more than ever.

    1. wa’ Alaykum As-Salaam, Gentle Soul 🙂

      I agree we can all relate better and love more selflessly and deeply. I think that most of us know these truths in our souls, sometimes all we need is someone to confirm what we already know or to clarify what seems unclear because of all the external noise around us.

  3. AvatarAvatarAvatarsays: Eric

    A lot of women get so angry so quickly if we approach them no matter how sensitively and thoughtfully we do it. It can be hard for a guy to make the move especially if he happens to be shy. I’m shy until a woman shows me she’s interested.

  4. AvatarAvatarAvatarsays: Wally

    I find it sexy when a confident woman makes the first move. Easy women on the other hand come on sexually straight away. Unless she’s really hot and I just want get laid, I’ll generally say no thank you. I don’t do it to hurt women, I don’t like leading women on.

    1. Hi Kathy, may be it’s a cultural thing… 🙂 I think however, there is a difference between pursing a guy and giving him hints/clear signals that say you’re interested. I’m not a guy but I can imagine how hard it is to read a woman’s mind…

  5. AvatarAvatarAvatarsays: Elliot

    I wish I wasn’t so shy. I postponed talking to a woman I was so in love with and someone else got to her before I could.

  6. AvatarAvatarAvatarsays: dave

    Love Doctor – With a divorce rate at about 50%, and women filing for 80% of the divorces ( supposedly mail order bride marriages come in at about 20% divorce rate since the young lady unabashedly says that she wants the guy)in our country, maybe women SHOULD be doing the approaching and living with more of the rejection.

    1. Where I come from, men approach women and women approach men without any fear of rejection — and relationships are generally more fulfilling and the divorce rate is very low. I’m sure there are many studies that explain the high divorce rate in your country. My personal non-scientific opinion based on my working experience is that a change in the way both men and women look at men-women relations, sex, love, relationships, marriage and divorce might help.

      Never seen men and women fear rejection and be so distrustful of the opposite gender so much as in North America! And the ones that talk (and complain) the most, fear the most.

  7. AvatarAvatarAvatarsays: Marci

    You have great advice for women and men. I think that if more men and women understood and practiced better ways to deal with each other, this world would be a much more loving place for us and for future generations. Thank you for your contribution.

  8. AvatarAvatarAvatarsays: Jenny L

    Thank you for your quick response. I have to admit, I am smitten and very much hoping he will call me. I won’t do anything rush and I’ll try not to jump to any conclusions but if he does call I’ll have a few questions for him.

  9. AvatarAvatarAvatarsays: Sinitta

    I just started seeing this guy a couple of weeks ago. He seems to like me and I think I’m falling for him. Friday we went out on a date. He told me to text him when I got home safely. I sent him a text as soon as I was in the house. I haven’t received a response yet which is really weird because he was always really good about texting, emailing or calling me back. My gut is telling me something is wrong. I’m trying not to be clingy but I just want to know where I stand.

    1. It’s normal for most men and women in the initial stages of meeting someone to step back a little if they’ve been spending a lot of time with that person. I personally think it’s a good thing for someone to “pull away” for a while to evaluate his/her feelings because when he/she does re-engages it’s because he/she knows that’s what he/she really wants. Try not to jump to any conclusions or do anything rushy. Give it a week to let him contact you. If he does, great, if he doesn’t try to reach out to him one more time just to make sure he is not ill or something worse. If he doesn’t respond, then perhaps he is not interested or is at a stage in his life where he does not want a relationship. It’s hard to say.

  10. AvatarAvatarAvatarsays: loulou

    I have also liked a guy for a year and a half and am positive he really likes me back. The problem is we see each other quite often but for such short periods and never alone. I’m too shy to ask him out and fear he’ll never ask me. Rejection would be better than this frustration because atleast I could move on. Any suggestion?

    1. If he’s not asked you out after a year and a half, he probably will not. So ask him out for coffee or a quick lunch (nothing formal) and give him the opportunity to get to know you away from other people and for a little longer period of time. He may turn you down but as you said, rejection would be better than the current frustration.

      On the other hand, you might actually be pleasantly surprised if he’s been waiting for you to make the first move. Guys find women who make the first move without being too aggressive, pushy or needy quite attractive. It shows confidence.

  11. AvatarAvatarAvatarsays: Nanabeats

    I’m very attracted to a very shy but he won’t step up and ask me out. I have given him every nonverbal signal that I am attracted to him. There is a possibility that he may not be that into me but may be if he knew how I feel about him things will be different. Should I keep on sending him signals and hope he gets the hints or tell him how I feel? I’ve known him a year and half now.

    1. A year and half is a long time. Like you said, there is a possibility he gets the hints but just not interested. You don’t sound like you just want to walk away without finding out. I personally don’t think sending him more signals will make him get it. I suggest you use a direct approach like “I really like you and would like to get to know you better”, and see where the conversation goes from there.

  12. AvatarAvatarAvatarsays: Indy

    Here is a quick update… I’m the woman who asked the question and wanted to be kissed already. I invited him to one of my dance classes and after the class he pulled me towards him and KISSED ME 🙂 It felt very special. Thank you for your wonderful advice.

  13. AvatarAvatarAvatarsays: Brad

    When I’m interested in a woman I tend to feel self conscious about things like if my zipper was down or if something was on my face. I’m too nervous to make the first move.

    1. It’s a “technique” I’ve read on pick-up artists/players gamebook. The goal is to “lower a woman’s value” and when she’s feeling vulnerable, prey on her insecurity. It mostly works with women who are terribly insecure and have very low self-esteem but not with a confident secure woman — a guy tries to “lower her value” and she just walks the other way.

  14. AvatarAvatarAvatarsays: Seol

    Re: faye’s comment. I do think that avoiding someone can be a sign of interest. I know I occasionally do that as I am sometimes too scared to bump into the woman I like and don’t want her thinking I am stalking her or something.

    1. I hear what you’re saying Seoldude. Avoiding someone you’re interested in because you’re afraid of making the wrong impression is different from always ignoring that person and talking to other girls with the intention of making her feel insignificant. My guess is that if you were around many other people, you’d at least make an effort to talk to her even if you didn’t know exactly what to say or can’t speak much because you’re shy. You wouldn’t deliberately ignore her or be mean to her.

  15. AvatarAvatarAvatarsays: faye

    the same here with me. from the moment i have seen him, he has always ignored me and talked to other girls but not me, even with the one who i am with so i always end up at the background. i recently found out from my friend that he said that when he likes a woman or finds a woman attractive, he ignores him so that the woman may become challenged with him. this is what exactly happened to me right now. i feel like i should pursue him since i am also challenged with the way he treats me. should i be friendly with him or be mean back to him? what do you think.

    1. I don’t mean to be rude, but how old are you both of you? The “finds a woman attractive, he ignores her” is so high school. Your guy is NOT SHY, he is immature. Now you are asking if you should be mean back?! The only thing mean breeds is mean. I think you should ignore the “ignoring you” and go on with your life. As for pursuing, how do you pursue someone who ignores you? Something toxic about your attraction to each other — never ends well.

  16. AvatarAvatarAvatarsays: SweetB

    I’m in a similar situation as you Lorelei. It’s so very frustrating especially when you know he likes you but won’t do more than stare.

  17. AvatarAvatarAvatarsays: Jason

    I can communicate with women confidently, initiate talks but I feel a bit of anxiety when talking to a woman I am attracted to.

Leave a comment
Leave a comment

Your email address will not be published. Required fields are marked *