Webster: Flying ... wannabe pilot.
Monica: I would have an “enhanced spidey sense” to easily identify weird or wacko people.
Webster: Man is thawed out after 25 years of not dating. Re-enters the weird dating world clueless.
Monica: Girl meets boy. But boy is totally self-absorbed. So girl pursues boy until she “catches” him. After which, she becomes bored. Then she moves on to a new challenge! Ad infinitum ...
Webster: Athletic/active, thin to small average, educated, secure.
Monica: I only date fit or athletic men.
I don’t limit myself to any particular race or religion. The men must have a sense of humor ... and a job.
Webster: Being outdoors.
Monica: Cycling from Maryland vineyard to vineyard. Traveling. Well-read.
Webster: Someone who can laugh at themselves, someone who understands all of us are funny in some way.
Monica: Dave Chappelle (with a touch of sarcasm).
Webster: Her career.
Monica: More flexible schedule. Less stressed.
About the date ...
7:30 p.m., Black’s Bar & Kitchen, Bethesda
Monica: I’ve been on dates before, so I wasn’t really nervous. What I think is funny is the reaction from everybody — “Oh, my God, you got in?!” Everybody’s very, very excited about it, which is cute. I have friends critiquing the outfit: “Well, if you’re taking pictures, you want to make sure you have nice jewelry at the top.”
Webster: I guess we’re all looking for somebody, but I didn’t get my hopes up too high, like: This is going to be the end-all person. This is just another adventure in the dating game, the way I see it. I was looking forward to having fun. I got there about 10 minutes before 7:30. She wasn’t there. So I went to the bathroom.
Monica: I was ahead of schedule. I went in, and he wasn’t at the table. So the waiter took me over to the table and then [Webster] came over.
Webster: When I came back, she was there. She’s definitely attractive. She looked really great, from the physical aspect. And she’s athletic.
Monica: I was pleasantly — not surprised, but I was pleased. I like the fact that he’s tall. That’s very important. We both gave positive responses.
Webster: She was pretty upbeat, so it really started off pretty good — good conversation.
Monica: I think we’re both upbeat personalities, so we started just chatting. I think he started asking questions of me first. We were looking at the wine lists and talking about what our tastes are in terms of food and wine, ’cause we were figuring out the meal as well as getting to know each other.
Webster: It took us a long time [to order], ’cause we were there yakking. It was not like an interview, but still, we wanted to feel each other out. There was a lot of laughing in between. It was lighthearted but informative. We both stayed away from [career conversation]. We weren’t interested, and maybe that’s an age thing. You know, at this age, you don’t really care what you do — as long as you’re working.
Monica: As we talked, I think we found a number of things in common. I sort of like to analyze, so I was trying to figure out what the match points were, and I think that there were a number: humor, working out, fashion. And we both ask a lot of questions. Usually I’m the one doing all the asking. But he was as much as me.
Webster: We found the exercise thing — we both like to work out. We definitely want our partner or mate to be active. She has a sense of humor and I do, too. Hers is somewhat sarcastic and mine is somewhat dry-sarcastic, so we kind of got each other. It was very warm. There was nothing fake about it. It was like we’d been out before.
Monica: We both did a lot with the camera. We even interacted with other patrons. There was a couple at the table behind us that had met on eHarmony. We kind of explained why we were there. Then they shared their story, and we talked a little bit. Then they came over as they were leaving to kind of give us a little pep talk. It was fun.
Webster: It’s hard to say [if there was flirting]. I was a gentleman, and she was definitely a classy lady. But when we took pictures, it wasn’t like we were standing apart from each other. We were actually kind of hugged up. I don’t know if that’s what you’d call a flirt.
Monica: Absolutely, those were flirtatious moments. It wasn’t artificial. When there was an opportunity or a moment when it seemed appropriate, I think we both did.
Webster: There’s definitely, definitely chemistry there — definitely. We closed down the place. I think we got kicked out of the restaurant around 11:15.
Monica: We went to the garage, and I think that’s where we exchanged phone numbers. He asked for mine.
Webster: It was funny, because at first it was like, “Well, okay, see you later.” Handshake. And then I said, “What, not even hug?” And then we did hug.
Monica: I’d [rate the date] 3 [out of 5]. I think you guys did a good job of matching. It was pleasant. But overall, I don’t think there were sparks.
Webster: I’d give it a 4. She’s a very classy lady, which I like. A very charming lady. And someone I would enjoy being a friend with, if it didn’t proceed to something other than that. I like hanging out with her.
UPDATE: Webster and Monica went out for sushi the following Saturday night. Conversation flowed, but it became apparent they had different priorities. “She’s more career-driven, and I just want to enjoy life,” Webster says. We had a hard time just getting her on the phone for an interview, but Monica says her schedule’s not to blame for the fizzled chemistry: “For the right person, I’d maneuver around it,” she says.