Correction: Print versions of this column misspelled one dater’s surname. He is Jeremy Rutter.
Jeremy: “First In: An Insider’s Account of How the CIA Spearheaded the War on Terror in Afghanistan.”
Rebecca: I stick out a lot. I don’t have a black North Face jacket; I enjoy colorful clothing rather than wearing black all the time.
Jeremy: I’m not a terrible driver, and I’m not a Caps fan.
Rebecca: Tall, dark hair, relatively fit, funny, smart (college-educated), Caucasian, chivalrous, has a job and has a car.
Jeremy: Tall, slim and athletic. Great smile. Is comfortable (and looks good) without makeup. Mature, settled and intelligent. Easy to talk to and open to trying new things.
Rebecca: Outdoor sports — running, rock climbing, hiking, kayaking, snowboarding. Likes reading, works out, passionate about their work or at least enjoys what they do, interested in having a family someday.
Jeremy: Racing, jets, space, baseball, travel and current events.
7:30 p.m., Portofino, Arlington
Jeremy: Heading to the date, I was pretty nervous. I got to the restaurant 10 minutes early. She was about 10 minutes late, so I had about 20 minutes to sit there and plan it all out. Like, When she walks in, I’m going to do this, I’m going to say this. I saw a girl walk in and was like, Okay, here we go, but it wasn’t her. That happened a couple of times. It was kind of funny but really nerve-racking. I read the wine list over and over. I was going to wait to get a drink, [but] I ended up getting a glass. She showed up at 7:40.
Rebecca: I was really tired and had to come from work. I wanted to have to something good for the evening because my day had been so bad — and long.
Jeremy: At first I was thinking, Well, she’s kinda late, so that’s not good. I did read one Date Lab about the lady who got stood up, and at some point, I thought, What happens if I get stood up? But it turns out that she was driving from Baltimore and had to deal with traffic. So it wasn’t a big deal.
Rebecca: He stood up from the table when I arrived, which I liked, and my first impression was: Whoa, he’s super tall.
Jeremy: I am 6’3”. I’m the guy people ask to help them at the grocery store to get things off the top shelf.
Rebecca: I love tall guys, so that was good. He was very handsome and had a muscular build. He was excited and looked relieved that I wasn’t some crazy person. And he was really nice in welcoming me. He didn’t badger me about being late. I was so embarrassed about it.
Jeremy: My first impression was good. She was dressed nice. I liked her hair. She hates her hair. But I liked it. We got through the normal stuff: jobs, family, where we’re from, where you went to school. The conversation didn’t really slow down throughout the night.
Rebecca: I am from California; he’s from Florida. We were both talking about how it made us miss the good weather. We both have lived in a lot of different places, with different kinds of cultures, different kinds of attitudes, and we both agreed that we liked this area.
Jeremy: I was more curious to why we were set up. She said she was looking for a tall guy. And I said, “That’s funny, because I was looking for a tall girl, so at least one of us got the tall date.” I’ve never really dated tall girls before, but tall girls are attractive, so that’s why I put it on the questionnaire. We were joking about her 5’ 5’’ being “tall.”
Rebecca: We [didn’t] look at the menu for a long time. We ordered in rounds, because we were never really ready when the waiter kept coming by. [Jeremy is] a little younger than me. When I mentioned how old I was, there was slight pause. Not a big reaction, like it was big deal; I could just tell he was thinking that over.
Jeremy: I wasn’t surprised that she was older. It wasn’t a big deal.
Rebecca: During the date, I was thinking that it would be good to go out again. Chemistry? That’s harder to say. He is nice and attractive. Do I know if I want to date him forever? Who knows, but I would like to see him again and at least be friends.
Jeremy: The conversation didn’t drift toward flirty. I wasn’t sure how interested she was. I am a bad judge of that. I’m not sure we really clicked romantically. Sometimes I’m too picky. I make up my mind too quick. But I definitely have been on dates or met girls and known immediately that I want to take them out again. I don’t think I had that feeling last night. There was a time when I distinctly remember saying to myself, “I need to start giving things a second chance and not be so quick to give so much weight to a first impression,” but I haven’t really followed through on that. It’s just who I am.
Rebecca: We had desserts. Their rum cake didn’t compare to mine. We were joking that it didn’t have enough rum in it. But we’d had two glasses of wine, so we were good. He walked me to my car, which was super nice, and asked for my number. We hugged. I’m not someone who usually kisses on the first date.
Jeremy: I asked her for her number. I give it a 4 [out of 5]. It was a good date. I would like to hang out; I just don’t know if it’s a long-term relationship kind of thing, and I am looking for that, I think.
Rebecca: I’d give it a 4. I had a very good time, and my uncle, who is in his 70s and suggested I do this, is going to be thrilled.
UPDATE: They traded texts after the date. “We agreed that we both had fun but didn’t talk after that,” Rebecca says. At press time, we asked Jeremy if he thought he might break his picky habits and get together with her again. “I had a feeling this question was coming!” he said. “Perhaps we might hang out in a more casual setting after the holidays ... maybe meet her and her friends at a bar for a drink or two and then take it from there.”
UPDATE 2: We checked in again a few weeks later. Pickiness wins out, it seems: No contact for Rebecca and Jeremy since we last spoke to them.