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Got Another Lady Question to Ask You All


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I'm sure you guys are getting sick of these by now, but I just can't post this stuff on social media because I don't want too many people knowing my business. And since the other message boards I used to frequent are now defunct, you guys are my go-to. Lucky you.

Anyway, this one will be brief, and is more of an annoyance than a serious thing. There's this newish girl at work who I started flirting with almost right off the bat, and I've asked her to lunch twice (which she obliged) and have gotten her number. However, she's quite a bit younger than me--she is twenty-one and fresh out of college, and I am thirty-five. She's a party girl and that is a big part of her life, whereas I am more stoic. It felt kinda weird knowing these things about her, but there is something about her that I can't quite put my finger on.

Anyway, what interest she may have had in me seems to have fizzled out, as can best be illustrated by our company golf outing/drinking event this past Friday. I went over and talked to her when she was on her first drink, asked her if she wanted to hang out that evening, and her reply was less than committal. As time went on, we'd seldom see one another. The worst part was when she'd visit my table and not interact with me, and that just soured my mood. The fun was killed, although I think I faked it pretty convincingly.

So here's the thing: I know what I need to do. I know I just need to move on from this, and I have every intention of doing so. Since it was not anything remotely serious, that should be pretty easy. I guess it's more of a "damn-so-close" moment. But my question is, does anyone have any advice on a good Hail Mary pass before I walk away? I know the odds are stacked against me, but is there any way to bring it up and be like, "Listen, I can read the signs, but here's what I think"? I figure I've got nothing to lose.



[EDIT] One thing to note, and it is a big one: she was referred by her best friend, who works for our company, and she spends any time she can with this friend. This is a girl I kind of have an odd feeling about, like she's not very inclusive, or at least has never been toward me. When this friend went on vacation for a week, that was a week when I really got to talk to her, to walk out of the building together and whatnot. She was with her friend most of the time at the drinking event.

I think I overthink things, in case it wasn't obvious. It just makes me feel so old, where a young party girl might perceive me as boring. My friends insist I'm not boring, though.

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To a 21 year old, anyone over 30 is boring. It's not just you.

 

Move on.

 

Also, most 21 year olds are useless in the sack anyway. You'll spend more time coaching them through neurosis and getting them relaxed to actually have any mutual enjoyment out of it. Anyone that thinks they were a decent lay at 21 doesn't have a clue what they are talking about.

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Are you super rich or more handsome than Brad Pitt? If no, get over it and accept that she's not into you and 21 year olds won't be.

 

If you are super rich and/or more handsome than Brad Pitt, get over it and go for another 21 year old if that's what you want.

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The other thing is, this is work. Is trying to be with her worth getting fired? Because pursuing her at this point could definitely be taken poorly and the culture is changing. At my job, people have to sign a form before they can date anyone from the office with both people agreeing it's mutual.

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Well, I work at a place that's pretty laid back where the management don't care so much about personal conduct as much as most places, as long as it isn't ridiculous. With that said, the handbook does say that should two employees enter into a romantic relationship, they ought to inform their supervisor(s), and the supervisor has the right to make the judgment call as time goes on as to whether or not it's becoming problematic and take the necessary disciplinary actions, up to and including the termination of one or more parties if it's really getting out of hand. However, I seriously doubt they'd follow it, or at least my sales manager probably wouldn't.

With that said, I've not disclosed it to anyone. People have seen us out together, but that's not grounds for suspicion. There's not been any PDA or anything like that.

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People have to sign a form to date? That's pretty crazy

I work for the government. I'm surprised I don't have to fill out a form to take a dump.

 

Well, I work at a place that's pretty laid back where the management don't care so much about personal conduct as much as most places, as long as it isn't ridiculous. With that said, the handbook does say that should two employees enter into a romantic relationship, they ought to inform their supervisor(s), and the supervisor has the right to make the judgment call as time goes on as to whether or not it's becoming problematic and take the necessary disciplinary actions, up to and including the termination of one or more parties if it's really getting out of hand. However, I seriously doubt they'd follow it, or at least my sales manager probably wouldn't.

 

With that said, I've not disclosed it to anyone. People have seen us out together, but that's not grounds for suspicion. There's not been any PDA or anything like that.

I'm not talking about a relationship being a problem, I'm talking about pursuing a relationship with someone who doesn't want one. What you may see as innocently inquiring, she could easily see as her having given you signals to back off that you've ignored. Now you have, unintentionally, created a hostile work environment for a young girl starting her career.

 

I'm not saying you're a monster or anything less than a great guy, but there are different perceptions and you need to be careful when you're dealing with your career.

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You can try being friends with her for months and even years, and hope that maybe-just-maybe she'll eventually begin to develop deeper feelings someday, but that sort of long game rarely works outside the world of sitcoms and tends to turn dudes into bitter monsters, among other catastrophic side effects. Not recommended. At all.

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Yeah, to be honest, I know she definitely is not "the one." I've had feelings like that about girls before, but not her. Basically, I see her as a really cute girl with a charming personality with whom I would love to have a relationship without expectations. Basically, I think she'd be fun. It would be a fun casual, non-serious relationship. I don't mean casual in a purely sexual sense, just in a more . . . high school way. I guess part of me misses that. She sort of reminds me of those days: no expectations, no pressure, just have fun.

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