Who should make the first move? - weird situation

I'm 45, unhappily married, two kids. "The girl" is 20, has a boyfriend.

Her and I met when hired to work at a start-up company. Her and I immediately hit it off and we both absolutely love each others company. The start-up flopped but her and I enjoy each other so much...and have a great deal of professional respect for each other (she's REALLY bright and talented)...that we're starting another business together. Her & I have acknowledged to each other; we bring an energy and inspiration to each other that neither of us are getting elsewhere. And we enjoy it.

On the other hand, there's an unspoken rule that nothing could ever come of us because of, primarily, our age difference. Or at least I think the rule exists.

Now here's the problem; we're hanging out (working) together a lot. And we look forward to it. While working her & I have the deepest, most fulfilling conversations ever. It's amazing. When our work time ends we're excited to complete our action lists and meet again. Often there are the deep stares, the deep breathes with the look in her eyes (and sometimes mine) that begs the questions; "What's on your mind?".

I know her current bfriend is her first and only lover. They've been together 5yrs. I know she loves him, but I'm beginning to wonder if she's become curious about other men. They broke-up briefly and she dated a bit, but nothing ever came of those dates. Our "work dates" are like dates because they usually take place at a coffee house or an eatery.

I want to get closer to her; emotionally, physically, or both. But with our age differences there's a very fine line between being nice and being creepy/pathetic. I'm afraid if I make any moves that she will push me away. That cannot happen because I want her in my life...at SOME level. On the other hand, what if she's having similar fears and is waiting for me to make a move?

If we were closer in age I would have no problem talking to her very openly about this. But because I am so much older I feel the need to be cautious.

Any suggestions?


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Most Helpful Girl

  • First...why would she like a old guy who can't even get it up anymore...you should leave her alone.

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    • Idk maybe he's rich? If you're rich like go 4 it. but like if your poor leave the girl alone like I agree with my friend here like why would she like a old guy who can't even get it up anymore

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    • No more fetishes, but I have a talent...I can easily spot old creepers... ;)

    • No you can't. You're not smart enough.

What Girls Said 2

  • U don't have to be smart to have that talent...U just have to be a girl...I am sure that bitch will start ignoring you soon <3

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    • "I am sure that bitch will start ignoring you soon". We just incorporated a company (she paid half) so I doubt what you say. But I'll let you know in a few months if you're right or wrong.

    • ok GRANDPA we have a deal

    • You poor thing. So immature. So uneducated. Let me guess: too smart for college so you're a clerk in a convenience store. What a stark contrast conversing with you vs her. Two extremes. Her's being smarts. Now like most immature 'lil girls, you need the last word. So go for it and I'll be in touch in a few months.

  • If not a creep, you're at least a coward.

    You should consider being separated from your wife before gazing into some 20-year-old's eyes over "business".

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What Guys Said 2

  • Yes, I know you don't want to hear this, but you're a father figure to her, not a lover, and always will be. While she might say yes to a sexual relationship, it would only be bacause she wanted to obey her Dad, believe me..

    She probably has complicated father issues she hasn't worked out. The best thing you could do is talk her though them, and if it gets too deep for you, advise her to get professional counseling.

    Gettinginvolved with her, from her side, would probably only deepen these father-fixations. And from your side, you'd be hurt when she rejected you for someone younger, which is inevitable...

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    • I agree w/the inevitable part which is why I keep my expectations in check. But please imagine for a moment that she has no dad issues. After all, you cannot believe that EVERY young woman yearning for an older guy has dad issues. She in fact has a great relationship with her dad and her whole family. Very healthy, stable family. She is a very sure-footed young woman.

      So with that said; who should make the first move in pursuit of that sexual relationship you mention?

    • If you're deerminedtogo ahead, at least have her make the first move so you can'tbe accused of manipulating her...

      If it's not father issues, it's her being a gold digger or something. There aren't 'good' reasons for this big an age difference.

  • Ever since the beginning of human existence women have wanted older men.

    If you both feel a connection, why not?

    As for her boyfriend, women "trade up" with males all the time. Nothing new.

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    • I almost forgot one more thing:

      Ever since the beginning of human existence men have wanted younger women.

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