Dateline: "Stylish green dress, great figure..."

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Male, 25, chemist
Female, 24, paralegal

6:30 p.m. - Arrive at a coffee shop called Crazy Mocha. Spacious but not very crowded. Decide to wait out front.

6:33 - Date arrives. Stylish green dress, great figure. Photos on dating site were accurate.

6:36 - Sit down with drinks. I've got iced tea, hers is iced coffee.

6:48 - My date explains one way she filters guys who write to her. She sees if they checked the box for some kind of graduate degree. "To tell if they're smart." To tell if they make a lot of money, too? What happened to just seeing if the guy used "their," "there," and "they're" correctly?

6:55 - Our drinks are nearly empty. The conversation is decent so far, but I can't tell if this date is actually going well. I haven't had dinner, so I suggest we get something to eat. She agrees. It's her neighborhood — important detail for later — so we go with her recommendation.

7:10 - Good venue. A bit dive-y but not dirty. I expect the food will be decent and the beer a few notches above Bud Light. Bonus: we get seats in a huge corner booth!

7:18 - Because she posted a photo of herself visiting Israel, guys often assume she's Jewish. She clarifies: Irish. The blue-green eyes and pale, pale complexion would agree. (FYI, I'm of Indian descent. Like Kumar, from Harold and Kumar.)  

7:42 - She says she has career aspirations, but for now she's content with making money as a "barely legal" for one of those law firms that specializes in personal injury and has over-the-top ads on TV.

8:20 - We're midway through eating and a couple beers in. The conversation is flowing well, and I'm trying to gauge her body language. We're sitting next to each other in this enormous booth, but there's two feet of space between us, and for the most part she's facing the table. Which says nothing about how this date is going, since the food's also on the table.

8:48 - She recounts a bad first-date story. She and the guy were hugging goodbye on a busy street and he grabbed her ass. I trust this story is her way of contrasting that date with ours.

9:30 - Turns out this bar has a trivia night. We're nearly done eating, but we decide to stick around and play. I can only assume the date is going well, or she would have excused herself. I use the restroom.

9:35 - I come back and hear that she's texted her roommate to meet us since the roommate likes trivia. Hmm? Okay, maybe this date isn't going that well. I tease her, "This date must be going really well if you want me to meet your roommate already!" 

9:45 - We attempt a cutesy trivia team name that uses one word from each of our dating-site user names. Go, Team SparkyCat!

10:10 - First round of trivia ends. She's impressed by how I'm getting most of the questions. "You should be on Jeopardy!" File that under "dramatic irony," because what she doesn't know is I've actually been on the show — and won. I just chuckle.

10:12 - "I have the hots for Indian guys!" Didn't see that coming. Followed by a brief dissertation on what traits — apparently predominant in Indian guys — she finds so attractive. Something about combining good looks with intellectual achievement and leadership in school activities like tennis, for example. Talk about painting with broad brushstrokes!

10:20 - Things are feeling flirtier, and we're sitting much closer together and brushing up to each other. I can say with some confidence, this date is going well.

10:25 - Her roommate shows up. She's a smart, cheerful girl... who totally kills the vibe we had moments ago. The conversation dynamic with three people just isn't the same.

10:35 - I'm barely in the conversation at times because the two girls are chatting. On the plus side, the roommate is providing some help in trivia.

10:43 - The roommate says, "I could get another beer, unless you guys want me to go." The silent stare-down from me doesn't get the job done. She remains.

11:12 - Trivia wraps up. We settle our bills and walk out. It's not clear if this date is over — or was it already over when the roommate arrived? The roommate is walking a few strides ahead of us both when I amble up alongside my date. She puts her arm through mine and grins at me.

11:13 - I say to my date, louder than needed, "Since it's still nice out, do you want to take a little walk? I'm new to this side of town. Why don't you show me around?" The roommate finally takes a hint and decides to walk herself home.

11:34 - After the stroll through her neighborhood, I walk her home. Outside her front door, I go for the hug. She responds and goes for the kiss. I push her up against the wall.

11:45 - Wait for the bus to get home. I'm fairly confident there'll be a second date.


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