Jordan Weiner, 24, Law student and marketing director
His perfect woman: Angelina Jolie as his secretary
Says he’s a catch because: He’s involved in local politics, enjoys helping people, and is in incredible shape.
Whitney McManama, 26, Real estate agent
Stranded on an island, she’d want: Champagne, chocolates, and tabloid magazines
Her perfect man: Ryan Gosling as a former police detective who writes crime novels
7:30 p.m. Joe’s American Bar & Grill, Back Bay
Dress to Impress Jordan: I went to Target to buy some black shoes and took a shirt from my sister’s boyfriend’s closet because I’m a T-shirt, jeans, and sneaker type of guy.
Whitney: I was at work until the date. I did change into “date night” clothes.
Jordan: I was excited; I really enjoy blind dates because you get to start fresh.
Whitney: I kept wondering whether I’d be able to control my facial expressions if he turned out to be hideous.
McHappiness Jordan: She was tall, blond, stunning, great physique, and I was telling myself, “Jordan, you better be on your best behavior tonight because Whitney is gorgeous.”
Whitney: I was relieved because he looked normal, and I thought he was cute.
Jordan: I asked what her favorite color was, and Whitney does not discriminate against colors. I discovered she has a secret passion for the No. 2 value meal at McDonald’s.
Whitney: We both love to cook and enjoy wine. Also we realized we share similar control issues when we are cooking in the kitchen.
Jordan: We both come from a large family and like boats.
Whitney: He’s into local politics among a lot of other things. We talked about what we like to do in Boston and what we do for fun.
Jordan: Sparks were flying and laughs were being tossed around like babytown frolics. It was like a roller coaster of emotions. I enjoyed her company – especially when I made Whitney smile, I thought I was in. Sometimes she’d give me a look as if I had 18 heads – then I thought she was not going to even give me her real number.
Whitney: I didn’t feel huge sparks, but that’s what I expected. First dates can be awkward, and I was a bit reserved.
Getting Cheeky Jordan: I totally tried to take her out to the closest pub. Whitney was not having any of it. I asked permission to walk her to her car. I was a gentleman and made sure I was always on the street side of the sidewalk.
Whitney: I had to drive and had work the next day. I was having a good time, so if the circumstances were different I definitely would have continued the date.
Jordan: I went in for the kiss and got the cheek. Total bummer, because I’m an excellent kisser.
Whitney: I gave him a hug, and he asked for my number, which I gave him.
Post-Mortem Whitney: A-
Second Date? Whitney: I think we’ll go out again.
Jordan: I really think if we were in a different element I would have had a better chance to impress her. We both have very busy schedules, but I’m very persistent and will keep trying for date number two.
GO ON A BLIND DATE. WE’LL PICK UP THE TAB. To apply for Dinner With Cupid, fill out an application at boston.com/cupid.