The 17 Things I've Learned After 7 Years of SingleDumb

Mere moments before her trip to the altar, my childhood best friend looked at me and said: "You've been single for seven years in New York City -- you need to write about that."

I have zero qualms about broadcasting my misadventures on the New York City dating circuit -- I even created an entire web series that is based on my escapades. But, single for seven years? That is just not true. I date. I've dated! I've been in relationships! David, that four month long OkCupid bout, Simon, the British guy with the British teeth, Ben, and our The Notebook-like romance we had in Cape Cod this summer that I still can't seem to shake off. And, a handful of others.

How is that single for seven years?

I kept pondering this whole single-for-seven-years thing, and then, out of the blue, my stomach took a glorious drop upon realizing that since I had never really seen a future with any of the men I had dated, you could easily argue that I had been single for seven years. I had stayed in unhealthy relationships with men who had treated me poorly, men who I had treated poorly, men who I didn't respect, men who didn't respect me, men who smoked cigarettes by the carton, men who I was not physically attracted to (but his mind! his humor! his cleverness!)... the list goes on. And, sure, I had had moments with all of these men, I had even fallen in love with two of them.

So, in the spirit of not being in denial (yet still optimistic), I've compiled a list of the 17 things that I've learned after seven years of being "SingleDumb."


  1. If a date is not going well in the first hour, you have no obligation to stay. Please! Take my advice: leave. It might seem rude, but it's actually very kind to both of you.

  • If a guy texts too much, pick up the phone or, rather, pick up your bike and go see him in person. I became way too text-friendly with one former fling and when I saw him in person, the familiarity felt completely unnatural and honestly, really strange. He was also so much funnier via text than in person. I remember thinking, where did he go?!
  • If a guy you are dating requires consuming a minimum of 3-5 drinks every time he sees you, he's either not that interested in you, or more likely, an alcoholic.
  • If a guy on a first date starts to play a game of one-upmanship with you, tell him that you are double-jointed in both middle fingers and politely say "Oh, Ivy League -- is that like a club sports type of thing?"
  • If a guy suggests going to a hotel in lieu of his apartment because "it is under construction," he probably has a GIRLFRIEND.
  • If a guy who has just broken up with you sends you a text message to ask you if your dying grandmother is doing "okayish," and then does not respond when you say that she has died, try to pretend like he never existed. Who? What was his name? "Okayish?" Not okay, dude.
  • If a guy starts opening up to you early on about his dark past, recommend a really great therapist for him.
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  • If a guy you are dating invites you to a super expensive concert that his friend is performing in -- a concert that you would normally have zero interest in attending -- and he does not offer to pay for your ticket: politely decline the invitation and suggest meeting him post-concert.
  • If a guy you are dating agrees to meet you with energy snacks and a "hey, you're doin' great!" at Mile 9 of the NYC Marathon -- the race that you are running in, somehow -- and he is not at mile 9 when you get there, do not pick up your phone and try to call him, just keep running, and maybe never call him again unless he has a valid excuse like "I started running in it too." (For a moment, please try to look past the fact that marathon runners can be kind of annoying).
  • If a guy you are dating gets arrested in New York City for smoking pot... Who gets arrested in NYC for smoking pot? Who?! Might be time to find a new gent with good karma.
  • If a guy admits to cheating on you with his sunglasses on, he is probably stoned or weeping. Translation: he is a coward for not looking you in the eye.
  • If a guy tags you in a group Facebook post, you are not a woman he wants to bang. Sorry.
  • If a guy you are falling in love with is five years your junior, it is OK. Really. Just don't tell your mother.
  • If a guy befriends a homeless woman on your first date, suggest meeting his other friends on your second date.
  • If a guy comes on too strong at the beginning -- he most likely will fall off too strong at the beginning too.
  • If a guy has an accent, like charm, it too will wear off.
  • If a guy you're with is not right for you, it's a lot less lonely to be by yourself and unattached.