Evan Barden didn’t go on his first real date until he was 25. Sure, he’d spent a year in a relationship, but playing the dating game? It was time to try it. He wasn’t looking for romance. He simply enjoyed experiencing new people, finding people with whom he had a mutual attraction. But he felt that dating wasn’t what it should be — fun. And that’s how the Winchester native became a dating expert.

Inspired by onetime Bostonian Gaby Dunn’s 100 Interviews, he created a list of 100 dates. Between July 2011 and June 2012, the New York-based writer/comedian went on just under two dates a week with 89 different women, two men, even a group of speed-daters. He documented each date on his website,

So what it is it like to be on a date with such an experienced dater — a guy who’s been around the block, so to speak? How does he act? What does he talk about? Is he more relaxed than your typical blind date? I’m in a relationship so I set him up with my friend Alana to find out. Here’s what went down.

10 p.m., her place

Evan: I haven’t driven in Boston in a long time. I got to her place a bit early and then drove around Boston for a while so that I didn’t look like an idiot who didn’t know his way around. It’s always smoother not to have to use your phone for directions. I pulled up outside and called her. It was funny to hear her voice before meeting her, you know? Because we all text so much these days.

Alana: He was really punctual — he picked me up at 10:01. When I went downstairs to meet him he was waiting outside of his car, I guess to make sure that I knew it was him so I didn’t get into the wrong one…which has happened to me before, by the way.

Evan: She came downstairs and she looked great. It was cold and I was all bundled up, but she was wearing fun date clothes. She was very friendly. She greeted me with a hug.

Alana: I thought he was cute, and well dressed. I really liked his beard. It was a cool beard. His glasses made him look smart. He seemed very confident. You could tell he’d been on 100 dates.

Evan: We went to the first bar (Lucky’s Lounge) and started chatting. She told me about school, about where she’s from (Puerto Rico). I gave her some of my background, what I’ve been doing with my life and my work.

Alana: He sat next to me instead of across from me. I told him I drink IPAs, so he went up to the bar and ordered for me. He was really sweet — he paid for all of my drinks.

Evan: We sat in the back and had beers and about halfway through a live band started playing. It was fun but we were trying to talk and it was way too loud, so we left to go to the second bar, Drink.

Alana: He was really easy to talk to — he talks a lot, actually — but not just to fill in conversation. We talked about everything, really. About the job that he just quit, about potential projects he’s getting involved with. We talked about the One Hundred Dates project a lot — that’s mostly what we talked about. I’m a lot younger than him (he’s 28, she’s 21), and it was interesting to see our different perspectives on dating and relationships — him having graduated a while ago and me being still in school. Totally different dating environments.

Evan: I thought she was very friendly. It didn’t feel like she was trying to impress me, she was just genuinely fun and friendly. She had a good attitude about the whole thing. I think that’s a big thing when the person seems like they want to be there.

Alana: We were sitting and talking at the second bar and a very intoxicated couple sat next to us. It was a pretty fancy place, so we had our tiny, delicate looking drinks, and we watched as the bartender brought the drunk couple this…chalice thing. But it looked like a pineapple. In a luau skirt (can’t stop laughing). Oh, and it was on fire. It came with a volcano contraption-shaped thing, which was also on fire. The man sitting next to us accidentally let the table catch fire, and the bartender patted it out with his bare hands. We were very confused. It was a conversation starter.

Evan: There were flames all over the counter. The bartenders were oddly calm about it, like it happened all the time.

1:20 a.m.(ish)

Alana: We stayed at Drink past closing time, until they basically kicked us out. Then we went to his car and kept talking. He drove me home and we parked outside of my apartment. I asked how long he was in town for, and he said he’d just come up for the night, for the date, so that was pretty cute and flattering. I mean he was obviously doing it for work, too, but it was still cute.

Evan: I drove her home and she told me to make sure that I see this movie, “Before Sunrise.” We said it’s time to go, it’s late … you know, we were delaying. We were about to hug goodbye but I pulled back a bit and went in for the kiss. I thought it was a nice date! I felt a little weird about it, I wasn’t sure if it was the right moment and for a second I was worried I had offended her, but I think it was fine. I sent her a text when I got home to let her know I hadn’t died. She seemed really happy.

Alana: I was about to leave and he goes, “So, see you never?” And I said, “No, I’ll probably be moving to NYC soon.” And then I went in for a hug, and he gave me a kiss! Bam. And that’s it. Oh wait, I also kind of invited him to Puerto Rico. To stay at my beach house. Actually, I definitely invited him. He texted me this morning, and we confirmed it.

Evan was definitely more relaxed and laid back than other guys I’ve met. You could tell that he was older, and that he wasn’t self conscious about what I would think of him. I think that comes with age though. What was interesting about our interaction was that we had a blank slate to start from. With other guys I’ve gone out with, there were mutual friends or shared experiences or something like that. But despite the fact that I’d never met Evan, he had a lot to talk about because he’d traveled so much and met so many people. He’s a really interesting dude. I don’t know if I would pursue a relationship with him, but I would definitely hang out with him again. If I move to New York, I’ll give him a call.

[Photo: Ian Stroud]