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DEAR ANNIE: I have a crush on my 18-year-old co-worker, and I’m certain she has a crush on me, too — even though I’m 42 and she doesn’t know my age yet. The age gap is too big, which makes me afraid to ask her out because I don’t want to ruin my friendship with her.
The last time I had a relationship with an age gap this big was with a 19-year-old woman when I was 33. Before that, I had a relationship with a 45-year-old woman when I was 25.
I’m not sure what to do. Transitioning our relationship from friendly co-workers to something possibly romantic is a huge step for me. But there’s a new movie coming out soon that I know she’s excited about, and it seems like the perfect chance to ask her out. But is it worth risking the friendship? And possibly complicating things at work? — Age-Gap Gambler
DEAR AGE-GAP: It’s important to remember that along with this woman’s young age comes a much different phase of life than the one you’re in. Your dating history makes you much more equipped than her to handle a relationship with such a significant age difference — and that’s assuming she is even interested in one.
A meaningful friendship can be just as, if not more, valuable than a romantic pursuit. It’s not impossible for this to eventually blossom into something more, but for now, I’d play it safe and focus on enjoying the friendship you two have built.
Send your questions for Annie Lane to [email protected].
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