Reflecting on (Almost) Three Years Single

Reflecting on (Almost) Three Years Single

Shortly after moving to New York City, a friend of mine asked me what it’s like to date here.

“Well, I’ve been single since the week I moved in,” I replied.

And it’s true. The day before the start of my sophomore year of college at Barnard, a transfer I now admit to having been as motivated by my then 2-yr-old long-distance relationship as it was by a tech startup I was helping build, I broke up with my boyfriend. I’d found out earlier that summer that he’d been having an online relationship with a former coworker of mine. I’d been in school in Oregon at the time, he was in Pennsylvania, she was in Arizona. He said that couldn’t afford to visit. Some email sleuthing (that I’m not especially proud of) turned up the fact that the reason he couldn’t see me, was that he’d bought flights to see her. Flights he never used, he argued in his defense. The fact he couldn’t follow through on seeing her somehow made it worse for me. If he’d really loved her, at least something real would have torn us apart, but it wasn’t love. It was young, and it was stupid, and I tried to forgive him.

It took me longer than I’d like to admit, just about the whole summer, to realize that in addition to volleyball and whistling, forgiving a cheater is something I’m not too good at.

Over the past three years I’ve dropped out of school, moved four times, helped to build and sell a company, developed my writing into some semblance of a livelihood, adopted a dog, joined the Board of a nonprofit, returned to school, and gone on a lot of first dates. Some were followed by second or third dates, and some turned into mini-relationships that fizzled out as soon as they sparked, but most ended the night that they began on a barstool in Brooklyn (or Soho, or…).

An interesting lesson that I’ve learned from all of these attempts at dating is: Google seems to be my biggest cockblock.

I’ve said it before, and I’ll say it again, I am scarily Googleable. You can’t Google me and say “oh well, maybe this is a different Pippa Biddle.” No. It’s me. About 50% of men take this as a secret weapon that only they have discovered. They’ll subtly bring up the last four articles I’ve written as conversation topics, or claim to have a passion for terrier mutts, impactful travel, and rare meat while simultaneously swearing that they’ve never stalked my Instagram. While I’d love to give them the benefit of the doubt, and they seem to have the best intentions of the bunch, I have a hard time taking any person that sees my online presence as a publically available user manual very seriously.

On the flip side, there are those who wait to Google me until after a first date. It is rare that I ever hear from them again. Perhaps, they get scared off or intimidated. Perhaps, it wasn’t fair to not warn them of what they were getting in to.

Most recently, I’ve encountered a third type of would-be daters – the men who know me well professionally, who like my work and seem to respect me as a businessperson, but who freak out when they realize that who I am when I have to be ‘on’ isn’t who I am all of the time. They say things like “I didn’t realize that you’re so weird,” and fail to muster even the slightest enthusiasm when I tell them about my pepper plants.

Out of all of this, I told my now exhausted friend, drained of all dating optimism, I’ve learned one really important thing.

“Which is?”

I’ve learned that I don’t need external validation of normalcy to be happy.

In fact, it might just make me a little bit disappointed in myself. I keep going on dates because if I sat at home alone as often as I’d like to, my roommate might get even more worried than she already is, but I don’t need to be dating someone to be fulfilled. Being told that you have worth by people who barely know you is actually, I’ve come to realize, pretty worthless.

And so, as I near my 23rd birthday, I also near the third anniversary of being single. I’m weird, I’m strange, I’m nothing like most people expect, and that’s just how I plan on keeping it.

See my more poetic and equally self-depreciating “Reflecting on (Almost) One Year Single”