About a month ago I went on a date with a nice Filipino boy. I met him on an app, but not a dating app – I actually met him in an Uber, making it a little less embarrassing, right? Maybe not. At first, the idea of sharing a ride with a total stranger seemed a little shady, but then I realized that Uber drivers are total strangers, so what difference does it make if a couple more strangers are added to the mix? So I gave it a try and now I have 10 new friends, including a guy named Murphy who texts me every couple of weeks an enthusiastic “Hey!”, a couple of Irish guys named Mike and Chris, a Real Estate mogul named Glen, an Analyst at Macy’s whose name I can’t remember but we’re definitely friends, and of course, Bae (Anthony).
I met Anthony in a Hyndai Sinata on a ride to a conference in Rosemont, which is a comically unromantic combination of car model and location. I’m not sure how we got to talking, but our conversation went on for entire 45 minute ride, with only a few awkward pauses. We touched on many topics typically discussed on a first date: origins, blood type, job, whether or not we’d ever been convicted of a felony, best deep dish pizza in Chicago, music, and of course, which Friends character we relate to most. Anthony claimed to be a Ross, but he’s a Chandler through and through. When we rolled up to my destination, the ultra glamorous Crowne Plaza Rosemont, friendly goodbyes were exchanged, but nothing more. I had a feeling this wasn’t goodbye. This was confirmed in the form of an unexpected LinkedIn request. This is modern romance, people. Girl meets boy, boy likes girl, boy hits her with a friend request on a business-oriented social network.
When I told my friends the story they laughed, but ultimately encouraged me to give him a chance. I asked them what my next move should be. Like, how does one go about flirting on LinkedIn? Do I endorse his Powerpoint skills or is that coming on too strong? We started messaging, and our conversation dragged on for about 4 weeks before he finally mustered the courage to ask for my number. We went on two dates, and while the spark just wasn’t there, I think he’s a really cool person. There was one really big turnoff about Anthony, and to be honest, it may have meant the difference between a third date…I hated his sunglasses. I’m being serious. They were circle frames, kind of like the ones sported by Mugatu, Nicole Richie, and Willie Wonka. That’s a fucking deal breaker in my book.