I Need Advice from Men 35-45

I have a situation that is driving me nuts! I am in my late 30s, divorced with a teenage child. I have I guess what you would call a crush on someone in his early 40s. He has two children who he is raising alone. We live in the same area so I see him almost everyday. He is constantly giving off the classic flirting signs, i.e. staring, gazing, smiles, small talk, etc. He has been doing this since last summer but it seems to have gotten stronger. Once I was talking to another man and he raced over to where I was standing to find out who he was. Another time I was talking loudly on the phone and I saw him eavesdropping behind a fence. I do flirt back by giving him eye contact and waving and saying hi to him. He is a VERY confident, outgoing person and I am totally confused by his signals and ultimately his motives. I feel like we are in grade school playing the staring game. This is so unlike his personality to be so shy. While it is sweet, I am getting frustrated by the whole situation. Btw, he knows I am divorced and I made it known recently to someone close to him that I am not dating anyone right now. I can't understand why he hasn't asked me out yet. Also, I am very shy and would never make the first move. Any advice from the guys would help. Thanks!


Most Helpful Guy

  • This easy. You live close by and you're a single mom? Next time you talk to him, stay standing there when there is a silence in the conversation, wait very calmly, make no move to end it, and wait for the talk to start back up. This is a signal that you want to be with him.

    Hey guess what? You need some help around the house! If only you knew a strong man who could drop over and spend a few hours working in your back yard (for example). You can't afford to pay but you would certainly be happy to prepare a home cooked meal for any kind gentleman willing to help you out. You could even reciprocate in kind and do some washing or cleaning for such a good samaritan.

    So he comes over to your place and spends a few hours helping you, then you go over to his place and help him. The important thing is that you never get nervous when there's a silence, you just stay where you are and wait calmly. This shows that it's not the words that are keeping you there, it's him. A calm silence will advance your cause better than nervous words.

    • Thanks for your advice. I'll keep it in mind. Your post made me think back to a conversation I had with him last year where we talked for like a half hour. He didn't want the conversation to end and I just stood there with my "duh" face on. The more I think of it, the more I see that he was openly flirting with me the whole time. I'd like to smack myself for not having the guts to give him more signals. Well, the good thing is that we live close by.

    • ....so hopefully this will just get stronger until he makes his move. I just hope he doesn't lose interest thinking that my shyness is a signal that I'm not interested. :)

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What Guys Said 1

  • How long has he been divorced? How long was he married? How old are his children?

    The answers to those questions could hold the key to your mystery.

    • I believe he's divorced about 4 years, probably married over 15 years and his kids are under 13 years old. What do you think? Thanks for your advice!

    • Show All
    • Yes, I just had a woman ask me out on Friday night. She had a good approach and said she would like to give me her number and I should call her some time. This is a really bad example because I was honest with her and told her I probably wouldn't call but I didn't make her feel like an ass or anything. It was someone that I knew from a while back and I didn't really have anything in common with. That's all.

    • I don't know if that makes me feel better or worse....lol. But at least you were honest with her. Some guys would have taken that as an opportunity for easy sex and then would have dropped her like a hot potato. Thanks for all your advice! :)

What Girls Said 1

  • Seems like both are you are gunshy about making a real move.

    Those other things you said are great, staring, gazing, smiles, small, etc but sometimes those are just signs a confident man gives to every person - especially grown men out of diapers. Anyway, nothing is going to happen until 1 of you becomes a grown up here and asks the other out. So if he's giving you all the signs, as you say, why aren't you slipping him your number?

    Tick tock - life's short.

    PS - I shouldn't give advice on this since I am in similar situation ;)

    • LOL about you being in the same situation. How is that working out for you? I have to say that I am shocked about this whole thing since most guys in my age group won't play games and just go for it whether they get rejected by the girl or not. Before this, I had never heard of an "adult crush". Thanks for your advice!

    • Um, I've had the same "adult" crush for two years.

      He made me have it because he did all the same things this guy is doing to you.

      Just recently we are able to speak with him finally not acting awkward and turning red. I think it's just when maybe a guy likes you so much they are super afraid of rejection or maybe we just think they like us, hell I don't know either and it sucks - I wish he'd make a move instead of stare and sly smiles and little "hello's"...ugh it's so paingfully annoying.

    • I had to laugh when you said "make a move" because I feel like making a t-shirt that says that and wearing it in front of him. Is your guy super confident other than with you?