This is the latest post from our Boston-based Date Reporter, Becca Strong. Catch up on her story here. In this post she talks about Her first HowAboutWe date.


I’ve never been stood up in my life, but I was pretty sure that’s what was happening.

There I was, just slightly overdressed for a rainy Thursday night at an intimidatingly empty bar/lounge. I wore my favorite pumps for confidence, but they weren’t working. Sitting in the corner booth, I perused the cocktail menu and pondered if I should order a drink before he got there. Better yet, I considered pounding two. After nervously checking my phone for the ten millionth time I saw that it was already seven minutes past.

I had begun messaging back and forth with Chris* on HowAboutWe a week or so prior, and it turned out we both lived in the same neighborhood. When we realized that neither of us had been to the new bar that had recently opened near our apartments, we decided to check it out. And now it was pretty clear he was not coming. At ten minutes after our agreed meeting time, I got a text message: “Running late, so sorry! Be there in a few.” Somewhat relieved, I waved down the waitress and ordered my standby glass of Prosecco.

When he arrived, he looked frantic and rushed — and much taller than I expected. “I’m so sorry,” he said, shaking his head. He gave me a polite, albeit nervous hug and explained that he had been dropping off a book for a grad school classmate at Harvard (score!) and she was running late to meet him. If ever there was a good excuse, he hit the nail on the head.

Chris was even more adorable in person. His photos were a little arrogant, so I wasn’t expecting the Ohio-bred, single-mom raised, midwestern gentleman mentality that became so apparent in our almost three-hour conversation. From his profile photos, he looked like a Romany Malco character that would have a crude sense of humor and player personality. It became increasingly clear that my impression was very wrong. Best of all, he mastered the balance of talking about himself and his own life and being interested in hearing about mine. He was fascinated with the fact that I was a writer, and when I admitted that I was having a blockage of topic ideas as of late he even began pitching ideas to me excitedly.

I probably could have kept talking to him all night but I remembered a girlfriend’s advice to me: “Don’t let the first date drag on too long. A couple hours max. Just a taste to give you both an idea if you’d like to see each other again.”

I admitted I was tired, and we left the now empty lounge to find it was still raining. Never unprepared, I shared my umbrella.

Since we both live nearby, it occurred to me that our exit might be awkward. Would he try to walk with me? Would we hug goodbye? Would he try to kiss me? Sure enough, he offered to walk me to my door.

“Listen,” I sighed, “I have to be honest with you. I’m not planning on going straight back to my apartment.” He cocked is head, confused.

“I have every intention of stopping at that convenience store on the corner and getting dessert.”

He was quiet for a moment, and then he looked up at me and said, “Well then, can I buy you a snack?” Never were more romantic words spoken.

And so by the light of the convenience store, Ben & Jerry’s pint in hand, he walked me back to my door with a promise of calling me. As I watched him walk away, he paused and turned around. ”I know this is against the ‘rules’, but I probably won’t wait two or three days to call you, either.”

Not one to play games, I smiled. ”I hope not.”

Becca Strong is a stylist by day and a writer/pool shark by night. She enjoys drinking bourbon or anything out of a mason jar and iced coffee in the dead of winter: preferably sub-zero temperatures. She was the captain of her Hip Hop team in high school, so don’t be surprised when she starts busting a move to Tyga unexpectedly. She’s still on the hunt for a man who loves dogs, knows how to make a mean chili and isn’t afraid to sing karaoke at the Hong Kong at 2am.

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