Jessica: When people first meet me, they see me as this nice, sweet girl that’s kind of innocent and naive. To some degrees, I definitely am. But then they learn that I’m an attorney and am actually pretty smart, and that I grew up with three brothers and am actually a tough cookie on the inside. I’m fiercely loyal to people that I love, and I have a huge heart. I listen a lot and ask provocative questions. I have a genuine zest for life.
Matt: I’m a stellar cook, I have all my hair, I have a great job, great friends, and my jokes can be biting and witty in the best way possible.
Jessica: I’m surrounded by people I love.
Matt: Being around old friends or after accomplishing something big. After finishing the marathon last year, I looked up and realized I had broken four hours. A couple of friends met me at the end, and I just broke down in elation. That particular race was especially emotional for me as I had started running ... to cope for losing my dad.
Jessica: Simply put, I need a man. I am actually pretty traditional in a dating sense, in that I like when someone holds a door for me and is otherwise chivalrous. I believe those traditions evolved over time for a reasons. I like to feel taken care of and protected. I prefer someone taller than me, so I can feel like a woman. Intelligence and maturity are really important to me. I tend to know what I want out of life and in most situations, and I would like the same from someone else. Finally, someone that has a zest for life like I do: always wanting to see, do, and learn more. The Jewish thing is actually pretty important to me, though I would be open to meeting someone that wasn’t, as long as he wasn’t diehard wedded to his own religion so that it would conflict.
Matt: Robin Scherbatsky [of “How I Met Your Mother”] stunning brunette with a career, a heart under a somewhat rough exterior [who] can hang with the guys but [is] a girl first and foremost.
About the date ...
7:30 p.m., Ceiba, downtown
Jessica: As I’m walking into the restaurant, he was walking in at the same time. I thought it could be him, so I kind of stood at the host stand and waited.
Matt: She was attractive and looked like someone I would go up to in bar or at a party. Not only was she really attractive, but I’d never seen her before. The Jewish community in D.C. is relatively small. Everyone knows everyone. So, to meet someone who I have never met before ... that was definitely nice. [Editor’s note: No kidding! Our original pick for Matt turned out to be someone he’d already dated.]
Jessica: He’s really cute. And for me that sets off alarm bells, when someone is too cute. Don’t get me wrong, you need physical attraction. And he was definitely physically attractive — tall, dark hair. If someone would guess what kind of guy Jessica would date, he would be the guy. But when I see someone is so physically attractive, I have to tell myself to watch out and make sure he’s also a good person.
Matt: We immediately started talking. The bread just sat there, untouched. She has a really interesting job with the city, and I’m very interested in city politics. Because I work at LivingSocial, I’m used to getting constructive criticism on the Web site, and she had some. The funny thing is that her criticism is actually something I’m working on — something I’m trying to fix — so that was good to see we share that perspective. I could tell we both have a healthy approach to life. She runs; I do distance running. We both like art museums, baseball.
Jessica: It was hilarious; during the same conversation in which we ordered wine, the waiter tried to get us to order a cocktail. Then, later, he did it again. He kept proposing odd drinks at odd times of the date. Neither of us were going for it. We were doing just fine with our wine.
He seems like a good person. He was telling me that his close friend’s fiancée is a vegetarian, and he tries so hard to cook for them so she feels comfortable and his friend is happy. He talked about raising money for a charity to run in a race. It’s too early to know whether or how strong romantically it could be, but as far as us having a lot to talk about and getting along, that definitely happened.
Matt: The conversation was bouncing all over the place. A little bit of an ADD conversation, in a very good way. We ordered dinner.
Jessica: He is very chivalrous. When I got up to go to the bathroom, he stood up! I go on a lot of dates, and I’ve never seen anyone do that.
Matt: The place started to get kinda quiet, and we were the only ones left. The only bars around there are the W and the Hamilton. Neither of us like pretentious bars, but she’d never been on the rooftop of the W, so we made an exception. It was crowded and extremely hot ... so we went downstairs and had a drink at the lobby bar. I wasn’t really ready to call it a night. I didn’t have meetings this morning, she didn’t have anything big either. So I said, “Let’s go to the monuments.”
Jessica: Who spends five hours on a date on Monday night if they’re not having fun? It was so random but so much fun.
Matt: I am really bad at reading signals. We were walking by [the Tidal Basin], and she said something about it being the most romantic place in D.C. And I was unsure what she wanted me to do with that information. Should I kiss her, or was she just sharing this fun bit of information?
Jessica: You know how you start to say something, and as you’re saying it you realize how wrong it’s going to sound? I realized that it probably sounded like a hint that I wanted him to kiss me. We both just kind of stood there wondering whether we should kiss then.
Matt: Like I said, I am extremely bad at this, so I erred on the side of respectable gentleman and didn’t kiss her. Not that I didn’t want to. We were close to where she lives, so I offered to walk her home. [Then,] I kissed her goodnight. Just a light kiss on the lips.
Jessica: From the beginning, I was thinking about [a second date]. The more the date went on, we just were having things to talk about and having fun. I’d give it a 4.25 [out of 5]. I am really curious about where this might go.
Matt: I had a blast. I definitely want to go out with her again. Date itself a 5, the match was a 4. I don’t know, it might be 5; I want to get to know her a bit more.
UPDATE: They traded texts, but when Matt spoke to Jessica about setting up a second date, he got denied. “She is more interested in being friends than seeing where things might go,” he told us. Jessica finds herself questioning whether they had as much of a connection as they thought. “I think we both just wanted the date to go well for the sake of the Date Lab article,” she says. “I have some other things going on right now, so the timing isn’t great for me.”