I Set My Ex-Boyfriend Up On A Blind Date

Most people don't speak to their ex-boyfriends. I played matchmaker for mine.
Publish date:
December 9, 2013
ex boyfriends, Dating, blind dates, matchmaking

Will and I met during November of my freshman year at NYU and immediately clicked. It was winter in New York, so we ice-skated hand in hand in Bryant Park, drank Serendipity frozen hot chocolate, and bought a Christmas tree together.

That spring, he invited me home to meet his parents. A few weeks later, we had a caustic break-up in the hors d'oeuvre aisle at Dean & DeLuca.

A few months later, we repeated the cycle. When we were dumb enough to date for the third time, he gave me a glittering crystal necklace for my 20th birthday in April. By that summer, I had fantasies of singing “We Are Never Ever Getting Back Together” at karaoke.

One night in July, I was sprawled across his bed while he worked on his laptop.

“What if we broke up?” I asked.

He stopped typing. “I guess we could do that,” he said with a shrug.

After more than a year and a half, we were over.

I had seen my friends go through horrifying break-ups, but this wasn't one of them. Will and I have the same taste in restaurant choices (any place with guacamole gets two thumbs up), wine (Jam Jar shiraz), and Netflix preferences (we're addicted to Mad Men), so it felt natural to stay friends.

The first few times we hung out platonically were tense. (Are we walking too close together? What if our hands accidentally touch? He'll know I wasn't trying to hold his hand, right? Right?) But by the fall, we had a groove going.

One of my favorite parts of going back to school in the fall was resuming “Now Kiss,” a blind date column I run for NYU Local. Students fill out applications online, and I match them up on blind dates. After their date, I interview each person and write about how the date went. My track record for successful dates isn't the greatest -– I recently set up a girl with her hook-up buddy's roommate -– but I've had a lot of fun as an amateur matchmaker.

Now that we're friends, Will and I trade stories about dating. I've casually dated a few people since our break-up, but Will's pursuits are always more entertaining. (A few months ago, he flew to Spain for a second date.) He goes on a lot of first dates, and a fair number of second and third dates, but few of them have panned out beyond that. One girl drunkenly accused him of being gay when he didn't immediately sleep with her, and then was so mortified by what she said that she refused to see him again. One seemed great on OkCupid, but not so bright in real life. Another was a Republican (he's a Democrat).

I've known him for two years now, so I know what he looks for in a girl. Could I set him up with someone better than he could find for himself? I jokingly proposed the idea to Will over coffee one day, and he took the suggestion seriously. Game on.

I had about 130 people in my “Now Kiss” database, which sounds like a decent number of options, but matchmaking is harder than you might think. Will is a Burberry-clad finance guy –- I couldn't exactly match him up with a pot-smoking artist. On the flip side, it would send a weird message if I set him up with my carbon copy. Age was also a factor. Will is 24, so I didn't want to set him up with anyone too young.

I chose Emily, a senior at NYU and a writer. She wrote that she can make conversation with just about anyone, a plus for a blind date. Her application was smart and funny: “Emma Stone would play me in a movie, mostly because of the red hair, but also because I like to think I could bed Ryan Gosling if I tried.”

Facebook-stalking revealed that we wore nearly identical champagne-colored gowns to our respective proms, both have a thing for red lipstick, and all three of us -– Will, Emily, and myself -– are total cat people. Unlike me, however, she's a baseball fanatic and grew up mostly outside the U.S. We look nothing alike.

There are very few ways to ask, “Would you like to get drinks with my ex-boyfriend next week and let me tell the entire Internet about it?” and appear sane, but luckily, Emily was interested.

“This sounds like a 'Sex and the City' column waiting to happen,” she emailed back. “I actually would be up for this!”

I set them up for drinks on Tuesday at 8:30 at Vintry, a wine and whiskey bar. I was surprised at how nervous I was on the night of the date. What if they hated each other? Or worse, what if they hit it off and I ended up personally choosing my successor? Later that week, I called each of them to hear how the date went.

I called Emily first.

“It helped that I had no idea who he was,” she said. “I had no expectations going in about his appearance or his personality.”

She was a little thrown off at first that he worked in finance –- she tends to go for more artistic guys. “I could see how he'd be a good fit in finance but there was also a lot more to him than just that,” she said. “He's from the Midwest and has two moms. I didn't expect that, which was awesome.”

They stayed at Vintry for two and a half hours, through three rounds of drinks and two plates of chorizo and cheese. There were no awkward silences and conversation flowed easily. Towards the end of the date, she wasn't thrilled that he pulled out his Blackberry and answered a work email.

I had been objective up until that point, but couldn't help but switch to ex-girlfriend mode when she mentioned the Blackberry incident.

“Ugh, I know, so annoying,” I gushed. Last spring, I felt lucky when he could pencil me in for 30-minute coffee dates once a week. I didn't need to be his top priority; I just wanted to be on his list of priorities, like his boss and his clients and the London office and the Tokyo office, and I didn't feel like I was. I rolled my eyes, tried to snap back into journalist mode, and continued chatting.

“I think we made sense on paper, but it's so hard to figure out who will click in person,” Emily said. “I could see us being friends, but I'm not sure about a second date.”

I called Will next. He said he doesn't typically get nervous before first dates, but then again, he's never been on a blind date before. I had given him her first initial and phone number, but that was it. He admitted to Googling her phone number, but that hadn't produced any useful leads.

Luckily, he warmed up to her right away.

“She's cute and friendly,” he said. Like Emily, he reported that the date went smoothly and he had a good time with her.

When I brought up her Blackberry comment, he backpedaled. “I tried to make it clear to her that I had to answer the email,” he said. “I wasn't on my phone because I wanted to be.”

The date ended on a positive note. “I got a kiss on the cheek at the end when I only went in for a hug,” he said. He'd like to see her again.

I might not have found Will's next girlfriend, but that might be for the best. Hearing about his dating life, including the girls he sleeps with, doesn't normally bother me. But hand-picking Emily made me nervous that they'd immediately hit off and have a better relationship than Will and I ever did. Setting them up made me feel a little like Amy Poehler's character in Mean Girls. “I'm not a regular ex-girlfriend. I'm a cool ex-girlfriend! I'm so cool about our break-up, I'll even encourage other girls to date him!”

Besides, it works to my advantage if Will is still on the dating scene. I can't wait to hear the stories he'll tell about the next girl.