True story, I went speed-dating right after my boyfriend rejected my proposal

The night my boyfriend Derrick announced he was moving to California to build an app, I did what any rational 29-year-old woman would do: I asked him to marry me.

He said no. Then we ate barbecue.

Things I know now:

1.When someone tells you they can’t be your boyfriend anymore because they’re moving across the country, chances are they won’t want to be your long-distance husband either.

2.Don’t propose marriage when hungry.

Somehow, even after such a traumatic event, my brain went on auto-pilot and helped me order pulled pork and something green — string beans, maybe collards? Derrick had a sandwich, which highlighted the “live cheap, travel light” start-up lifestyle pulling him west. I resented him for wanting to eat his meat between convenient slices of bread while I struggled to operate my knife and fork.

We’d circled each other in high school and reconnected in New York after college. We were both in relationships at the time, but used to spend whole (platonic) afternoons wandering the city. However, when we found ourselves single at 26, the switch flipped with a single goodnight kiss on the cheek. It got a bit too real too soon, though, and my skittish Sagittarius feet did a quick retreat. Three years later I came back for more, determined not to mess it up this time.

“I love you” has always been a hard phrase for me to get my mouth around, but Derrick has an asterisk next to his name in my book. Not sure why I’d expected things to work out now, but it sure felt different this time. It was like finding an old watch in a drawer and realizing it still ticks.

I have to hand it to him for being clear. There was no backpedaling to promises of phone calls or texts or bi-coastal visits. Not even a Let’s See What Happens. All he could say was, “I’m sorry.” In three weeks, we’d officially be friends.

I never once asked him to stay. I enjoyed what I could of our remaining time, and on the day of his departure, kissed him goodbye and locked the door. Then, I folded into ugly-cry origami.

My friend Kate had offered to take me speed dating that night — I had a feeling it was probably a horrible idea, but I also had a feeling it was too good a story to resist.

At 7pm I walked into the back lounge of a midtown Indian restaurant and checked in with the girl holding the clipboard. I wasn’t comfortable ordering my usual bourbon, so got a gin and club soda — a colorless, ambiguous drink felt safer, somehow. I could be any kind of girl holding a drink like that.

Everyone got nametags and scorecards. The women sat at designated spots and the men rotated every five minutes when a little bell rang. Everyone was supposed to mark off whom they’d like to see again. At the end of the evening, you’d go home, log onto the company’s website, and enter your choices. “Yes” matches would be sent each other’s email addresses to take things to the next level.

Date #1 man-spread across from me. “So,” he said, as if reading from a teleprompter, “what do you do for fun?”

Uh-oh. I’d been so focused on simply arriving with my mascara intact, I hadn’t even considered what the actual “dates” would entail, much less prepare stock answers.

“Um, fun?”

The look on his face said, “Not another career girl…”

I tried again. “Walking?”

“This is your first time?” he asked.

“What do you do for fun?”


A lot of these guys enjoyed similar things: the beach, beer, snowboarding, clubbing, watching sports. A few asked if I was ready to settle down. One aspired to relocated to suburbia within the year. Their sincerity made me want to cry.

Before I knew what I was doing, I was making things up, which was so unlike me. What did I do for fun? WELL! I hiked, painted, went dancing — it was oddly liberating to pretend to be someone else — someone who hadn’t been sobbing on her kitchen floor a few hours earlier. Maybe I was a divorcee. I was a psychotherapist. I worked in PR. I tested cookbook recipes. I was moving to California to work at a healthcare start-up. I totally dug movies.

My favorite part of the night was the 20-minute break, when the women congregated in the ladies’ room to trade notes: Who was sweet, who was slimy, who was sporting a glaring hickey…

With the guys, I struggled to stay focused. I had a fresh haircut, a red dress, and a neutral drink. Maybe if I laughed at the right moments, they wouldn’t notice the crumpled wad of paper where my heart belonged.

The final round began. Paul (or was it Neil?) sat across from me. He wore black pants and a black shirt with buttons straining up the front. He said he grew up watching movies in his parents’ basement and had perfected the terse art of handing coffee to snarling L.A. studio execs.

“So, Jess,” he said, reading my nametag, “do you think you met The One tonight?”

I laughed. “No.” My own honesty caught me off guard. I tucked my hair behind my ear and started over. “What I mean is, a friend brought me here. My ‘One’ just moved to California today, and he’s not coming back.”

A three-minute version of the story fell out.

“How old are you, Jess?” Paul-Neil asked.

“29.” The closing bell.

He patted my shoulder. “You’re brave to come out tonight. It gets better.”

As everyone juggled coats and awkward goodbyes, I shrugged and thought, “Well, I don’t see how it can get much worse.” I thought about “forgetting” my scorecard when I left but tucked it in my purse and promised myself I’d check “yes” a few times when I got home. I now had a “friend” on the west coast, and a whole new story to write.

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