Excuse me for the cliché here, but I'm allowed one Sex & the City reference, right? Remember that time Charlotte had back-to-back dates planned and it all blew up in her face? Well, that kind of happened to me accidentally a few weeks ago—but it wasn't a fiasco; it was kind of awesome.
I made plans on a Saturday night (something I normally don't do, but hey, I was free, and he was cute) to meet up with Casey. He was new to the city from Toronto, and via texting, he seemed normal and rather charming. He left it up to me to choose a place, which I usually prefer not to do. But because he was a NYC newbie, I gave him a break. Until of course, he texted me 10 minutes before our date to say he was just now getting in a cab and would be late.
Thirty minutes later when he was still MIA, I considered getting up and leaving, but I was having a nice banter with the bartender and relented. No joke, twenty minutes later, I finally decided enough was enough and headed out the door. I turned the corner to meet my friend Kristin for a drink, and I ran into Casey. He claimed he had been standing on the corner for the last half hour, unable to find the place (mmmhmm, sure) and he was sorry. I didn’t know how to just bail on him while standing face-to-face, so I led him back to the bar.
When we sat down and I revealed I was a writer, he was amazed. He said he wrote screenplays (and apparently for some movies I would know), in addition to being an investment banker on Wall Street. Then he threw out this gem: "But I write about things that matter. What are you actually contributing? And I don't believe you write more than five pages a day; I'm the only person who does that." Come again?
At that point, I was ready for the check and gave the bartender an eye—but as I excused myself to the bathroom and returned, another champagne cocktail showed up in front of me. The bartender had left the check (thank you for small miracles), and I instantly offered to pay. My date insisted. After chugging the drink down, I told him I needed to stop by the grocery store (yes, a lie), and he said he did, too. Finally, unable to stand one more second around him, I calmly told him that I wanted to go alone. I wish I could say I didn't run as soon as I saw him out of sight, but I did.
I snuck into a doorway to call Kristin again, and she invited me to a party in the neighborhood. I wasn't sure if I was in the party mood, but I felt strange wasting my evening, mood—and my outfit—on just some guy that pissed me off. I already had a date planned with a guy named Stephen on Tuesday, and though I doubted he was free on a Saturday night, I texted him just in case. I tried not to worry about how lame it made me look that I was asking for a last-minute date at 9 p.m., but when he responded 10 minutes later and said he could meet me in 30 minutes, I was oddly excited. And because I couldn't think of anything better before he caught the train, I picked the same bar I was just at.
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Stephen was one of those perfectly fine guys, and maybe it was because I was three champagne cocktails in or tired from date one, but I actually liked him. We left the bar and took up real estate on one of the comfy couches in the back, laughing about the same news articles, discussing why we loved NYC and which neighborhood was best, and sharing a same love for truffle mac 'n cheese. He was tall, blonde, and had a big smile, and when I went to order us another round—and appropriately swayed at the bar to Fine Young Cannibals' "She Drives Me Crazy"—he told me he liked my style.
That night, he walked me back to my door and didn't try to come upstairs. And as I crawled into bed, I was oddly really proud of myself for turning around a bad date into a good one. Sure, Stephen could have sucked, too, but he didn't—and while we didn't make it past a second date, it was refreshing to have that instant reminder that there is something better out there. Even if it's not the relationship, almost every really crappy date can be followed with at least someone you can tolerate for a few drinks.
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If nothing else, going on two dates in one night helped me see just how many guys are out there, and though I know ultimately (hopefully, for the love of all things good) one will be the right one for me, I often get caught up thinking there are no good guys left. So when a date is disappointing, I'm quick to damn all men to the land of impossible and lose sight on the gent that's most definitely in my future.
I’m not sure if I'd recommend double-booking on purpose a la Charlotte, unless you're sure you can swing it (what if the first date is awesome?), but a last-minute set-up after a sucky one might actually do you some good. And if you don't have the luxury of a dating app that finds who is near you, try simply flirting with someone at a nearby bar and seeing what happens.
At the very least, you'll really entertain the bartender. The one who witnessed my back-to-back dates later slipped me a note that said, "You can have two dates here anytime you like, the entertainment is great!" Curtain close.
MORE: 23 Things That Will Probably Happen on Your Next OkCupid Date
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Lindsay Tigar is a 26-year-old single writer, editor, and blogger living in New York City. She started her popular dating blog, Confessions of a Love Addict, after one too many terrible dates with tall, emotionally unavailable men (her personal weakness) and is now developing a book about it, represented by the James Fitzgerald Agency. You can find her running along the East River, drinking champagne with her dog Lucy (don’t judge), and constantly tweeting and instagramming. In addition to Dater Diary, Lindsay also writes for AskMen.com, eHarmony, Shape, Engagement 101, and more. E-mail her at lindsay@loveaddictnyc.com.
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