Rewatching ‘Clueless’ Has Made Me Into a Modern-Day Matchmaker

It’s no secret that I’m a massive fan of rewatching movies. (I do regularly recap the experience on this very website, after all.) It’s rare, though, that watching a film I’ve already seen upwards of 10 times teaches me anything new about myself—that is until I threw Clueless on one recent hungover Sunday. This time, the Los Angeles–set, Jane Austen–based rom-com planted an idea in my head: What if I got my Cher Horowitz on and started setting up people in my own life?

To be fair, this notion didn’t come totally out of left field. I’ve set people up before, most notably my dear friends Kate and Tyler, who I’m proud to say have been together ever since I wildly misrepresented each one’s level of interest in the other at a Brooklyn bar more than three years ago. (As it turns out, neither of them had thought much about the other in a romantic context, but they’re in love and living together now, so what was the harm?) Over the past few years, though, I’ve let my matchmaking skills atrophy, focusing more on my own dating life than the romantic needs of the lovelorn around me, and as I lay on my couch and watched spunky, irrepressible Cher do her best to bring joy and true love to her friends, I decided that needed to change.

Calling upon the long tradition of fixer-uppers before me—not just Cher, but also Carrie Fisher in When Harry Met Sally… (remember the little Rolodex of single men she tries to foist on Sally?), the grouchy matchmaker from the original Mulan, and Yente from Fiddler on the Roof—I worked together with a longtime Twitter pal to set up two of our queer single friends, both of whom just so happen to work in the same field. Side note: I think I’m particularly gifted at fixing up queer couples since I happen to be queer myself, and, to be frank, straight people often suck at this. (Just because your coworker’s cousin is also a lesbian does not mean I want to go on a date with her! Unless, I mean…is she cute?)

Bolstered by the relative success of that match (in truth, it might be slightly early to call it a success, since they haven’t met yet, but I have it on good authority that they’re texting), I threw out a tweet inviting my lovelorn mutuals to hit me up if they wanted to meet someone cute. Just like that, I was inundated with requests, and while I’m too much of a lady to share the details of my matchmaking, I will say I have high hopes for at least two of the pairs I had in mind. Only time will tell, I suppose.

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