Dear Tell All: I have a killer crush on a woman I work with. She’s beautiful and smart, not to mention generous and kind. She’s effortlessly cool in the way she dresses and carries herself. She’s funny, too, with a quick wit that’s terribly intimidating.
To be honest, everything about her is intimidating. Despite her sweetness, I’m scared to talk to her, worried I’ll say something stupid. Instead, I’ve mostly observed her from afar since she came to our workplace.
One thing I’ve watched closely is her interactions with coworkers. She’s naturally flirtatious with both women and men, so I’m not sure of her sexual orientation. I’m also not sure if she’s involved with anybody. She doesn’t wear a ring and always comes to work parties by herself, so it’s possible she’s available — though it’s hard to believe she doesn’t have suitors lined up around the block.
I’m a lesbian, and if I had to guess, I’d say she is too — though that might be wishful thinking. In my dreams, we’d go out for a drink on Valentine’s Day, open up to each other and fall madly in love.
I know it won’t happen, but at least I get the thrill of confessing my fantasy to an advice columnist.
Alone
Dear Alone: If you “know it won’t happen,” it most definitely won’t. But if you tell yourself it will happen, it just might. In other words, it’s time to stop observing and start acting.
For starters, why continue guessing about your coworker’s sexual orientation and availability? At the next work party, sidle up to her and start a conversation. If she’s as kind and generous as you say, she’ll forgive any initial awkwardness on your part. And if she’s as flirtatious as you say, she’ll respond to artful inquiries about her romantic status.
Depending on what you learn, your next step is to take action. If she’s single and interested in women, ask her out for a drink on Feb. 14. Life is too short to simply fantasize in the safe space of an advice column. After you two fall madly in love, I’ll expect an invitation to the wedding.
It’s true that things might not go your way, Alone. But since when was that an excuse not to strive for maximum happiness on this earth? Worst-case scenario: You have a decent conversation and move that much closer to a friendly relationship. I can think of worse outcomes for Valentine’s Day.
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