Kate Ryan, 32, physician
What do people notice first in your home? The absurdly high mirror above the fireplace
What would your exes agree about you? I have a good sense of humor.
Chuck Espie, 29, history teacher
What would you need on a desert island? Someone to laugh at my awful jokes
What makes you a catch? I always make people laugh.
7 p.m. 29 Newbury, Back Bay
Kate: I had worked overnight the night before, so the biggest thing I did to get ready was to get a couple hours of sleep.
Chuck: The weather was rainy, and I forgot my umbrella, so I went to the restroom to dry my face and hair off.
Kate: He was tall with a nice smile, but was maybe a little underdressed for the restaurant.
Chuck: Kate was quite tall for a female, pretty, and smiled a lot.
Kate: He is a high school teacher who just got back from Afghanistan. He was in the National Guard and worked with media personnel reporting from there.
Chuck: I learned about her job as a pediatrician, how she considers the parents her patients, too. I was impressed when I found out she spoke Gaelic.
Kate: We both coached basketball and were able to talk about that, but we had little in common.
Chuck: She told me how she took her shoes off to cross a massive puddle. The best part: She was proud of it as a Boston girl. I thought this was quite funny, because I was sitting there with soaked shoes and socks from the walk to the restaurant.
Kate: Chuck and I had completely different senses of humor. I didn’t find him funny, and I’m sure he didn’t find me funny.
Chuck: She had a good sense of humor, but I was not going to push the sarcasm too much on a first date.
Kate: We learned a lot about each other, but it felt like an interview. It wasn’t a painful conversation, it just wasn’t a particularly flowing one.
Chuck: I was able to ask her about a couple funny anecdotes about her job.
Kate: At one point, a waitress sprinted fairly loudly from one end of the restaurant to the other. When she did it again, I pointed it out. It was just so absurd, I thought it would be something we could share a laugh about. He didn’t seem to find it amusing. At that point, I knew it wasn’t going to work.
No laughing matter
Chuck: She is very interesting [and] attractive, but it would not be fair to lead her on. I live and work 30 minutes outside Boston. That, combined with her busy career, would make dating difficult.
Kate: At the end of the date, we were sitting there awkwardly, so I asked him what he thought. I was relieved when he said he didn’t think it would work.
Chuck: We gave each other a hug, wished each other the best, then walked our separate ways.
Kate: I wished him a safe drive home, since he had a ways to go.
Chuck: Kate was fun and interesting, but I do not think we made the type of connection that warrants another date.
Kate: We didn’t even exchange numbers. I have no idea what we would talk about.
--Compiled by Melissa Schorr.
Go on a blind date. We’ll pick up the tab. Fill out an application at http://www.boston.com/cupid.