The Hook Up: Work crushes and starting over

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I’m in my late 30s and have spent many years in denial about my feelings for women. While I am still attracted to men there are some women in particular who have always caught my eye. However due to my insecurities and fear, it has always made me stop short. Things changed when I started my new job. I noticed this one woman who stood out immediately, probably because at first glance I thought she was a cute young guy (she’s in her mid-20s). I would peek over at her from a distance whenever she passed by and she’d catch me every time. So one day she gives me a small tentative smile and I froze, then looked away. The physical attraction was instant and my heart was beating fast. I’m sure I was blushing because she gave me another small smile. Again I fumbled by answering quickly and going back to my work.

The problems is because I screwed her two attempts she kinda ignores me and when I try to engage her in any sort of small talk she’s just polite but not really friendly. I get why she’s acting this way because we’re both from the same Caribbean background where homophobia is rampant. She took a step and I did exactly what she was afraid of. So any advice on what to do or is my situation hopeless?—Shy Bi Chick

Anna says: I think so, yes! Now where did I put it—this post-it just says “Jason Priestley” and “buy Nutella” which always solves 90 percent of my problems, but probably doesn’t apply to your situation.

As to whether I’d apply the “hopeless” label to your foxy work crush, I can’t say because all I’ve got to go on is a few shy smiles and a little polite-but-not-overly-friendly small talk. Instead of parsing every detail and sidelong glance and lingering pause over the copy machine, I’d recommend you skip all that bullshit and ask her out to lunch. Don’t make it a date-y request. Make it casual. It’s just lunch, as that dating site is always telling me in emails I never signed up for. If that lunch goes well, ask her for coffee. Do this five to seven times, or however long it takes for you to learn things about her.

You know you’re attracted to her and that she’s Caribbean, which is a start, but just because she dresses in a masculine way doesn’t mean she likes to rug wrestle with the ladies. I mean, I hope she does, but we can’t say for sure. So go on, get to know her. Find out if you’re compatible, if you laugh at the same dry, British humor or enjoy the minor works of Macklemore. Allow yourself to be vulnerable. I know it’s terrifying, but it’s the only way to live. “If it doesn’t challenge you, it doesn’t change you,” as Fred Devito once said. He was probably talking about sit-ups, but whatever.

And congrats on your coming out. You’ve got some wild and exciting times ahead, so you might as well start as soon as possible, don’t you think? Let us know how it works out. Go team!

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