Welcome to an advice column by me, Sara Benincasa, a person with opinions. This column will not diagnose or “cure” anything. Hopefully, reading it will entertain and perhaps comfort you. Send questions to firstname.lastname@example.org or DM me on Instagram. If I use your question, I’ll edit it for space and keep you anonymous.
I have a crush on a woman in my recreational sportsball league in a midsize American city in the continental United States. I see her every week and we get along very well. I think she may be interested too. I’m very bad at knowing when somebody likes me back. (I usually assume they don’t.) How do I tell her? Should I tell her at all? I hate dating apps and really like that I’ve connected with somebody in real life. — A Shy Sporty Sporting Sportsman
Have I mentioned I sometimes take highly specific, detailed questions and anonymize them so people can’t be identified? YOU ARE WELCOME FOR “RECREATIONAL SPORTSBALL LEAGUE.” Anyway, let us proceed with a few questions.
Why do you want to tell her? Sometimes it is fun to just have a jazzy little crush that makes your heart go zippy zop in a non-afib kind of sexy way. But at other times, there is the possibility of dating a person. Ooh, saucy! Which brings me to our second query …
Do you believe this person is available to date? Is she single? If she’s not “single,” is she in some sort of non-monogamous situation that includes the possibility of dating humans, possibly even you? If she’s with somebody in a monogamous relationship, it would likely be best to keep your mouth shut, unless you reasonably believe she shares your feelings and would like to run away with you to Cancun and it wouldn’t, like, ruin everybody’s lives or something. Or maybe it would be fun to cause chaos in this manner, I have no idea, I don’t know your life! Also, why are you running away to Cancun specifically? Odd!
Are you willing to deal with all the possible results of confessing your feelings? If she does not share your romantic interest, will it make RECREATIONAL SPORTSBALL awkward and not-fun? If she DOES share your romantic interest, do you plan to ask her on A Date?
In conclusion, be cool, be polite, be respectful, and if she’s not into it, keep it moving. A fun fact is that I have a friend who went on one (1) date with a dude but was not feeling it. She was distracted and distant, and then she told him she wasn’t into him in a romantic way (because she wasn’t) and he was cool and friendly and just went on his merry way living life. She hated to have the conversation, as it was of course a little awkward. But because he was respectful and never pushy during their flirting and the not-so-successful date, she wasn’t at all worried about him flipping out in a nasty way (as women, we have many reasons to be concerned about men flipping out in a nasty way, lots of said reasons having to do with our own safety).
In other words, him behaving like a decent human led her to believe he could handle rejection. And, in fact, he could! They went on to see other people and touch base now and then about fun things (pretend this is about RECREATIONAL SPORTSBALL).
Then a couple years later she decided to ask him to coffee because she had gotten to learn more about him as a pal, and trusting him more made her think, “Has he gotten cuter? Have I gotten hornier? Hmm.” WOO BABY it was off to the sexy time romantic adventures!
Pretend this is golf and WORK ON YOUR LONG GAME. Is that a sports metaphor? I don’t know. Is not life a sports metaphor? Anyway, good luck!