There's no denying that Chicago is a great place to be single, but we could all use a break from the dating-app grind. Enter Dating IRL, an original Time Out Chicago feature that sets up two eligible singles on a blind date at a Chicago hot spot. After a night out, each dater reports back with honest feedback on first impressions, chemistry and awkward moments. This time, we matched Jeanette and Joe and sent them to Gideon Sweet for dinner and drinks. Let's see how it went.
RECOMMENDED: Do you want Time Out editors to set you up on a blind date? Apply today.
Grace DuVal
THE DATERS
JEANETTE, 30
Flight attendant, free spirit and kidney donor living in Lincoln Park
JOE, 31
Video editor, humor enthusiast and spontaneous dude living in Andersonville
FIRST IMPRESSION
JEANETTE
“Joe had a kind demeanor, but he came off as a little nervous. After swapping a few jokes, we were laughing and any nerves you’d get on a blind date were gone.”
JOE
“I was definitely more nervous than she was. I thought she might be a little quiet or reserved, but I quickly realized that she was just super chill.”
Grace DuVal
CHEMISTRY
JEANETTE
“I’d say we had a great dinner and our conversation flowed freely. However, there wasn’t a connection beyond that.”
JOE
“By the end, I think we had done a great job of listening to each other and getting a better understanding of what made each of us tick.”
AWKWARD MOMENT
JEANETTE
“A window broke in an alley next to the patio. That and the construction work going on at the same time made for constant entertainment.”
JOE
“My only semi-awkward moment was when I initially wasn’t sure if she was being sarcastic on a couple of occasions. Spoiler: She was! After that, it was smooth sailing.”
THE DATE SPOT: GIDEON SWEET
JEANETTE
“It was a great place to have small, shared dishes and delicious drinks. Our server was really sweet and attentive. I’ll be back!”
JOE
“There are a lot of food options, and we barely scratched the surface. We did get the sangria Popsicles, though, which was the right move.”
THE VERDICT
JEANETTE ♥♥♥ (out of 5)
“Spending the evening with Joe was enjoyable, and it’s always nice to meet new people. We had some fun moments, but it never felt like a date.”
JOE ♥♥♥♥ (out of 5)
“I had a great time getting to know Jeanette. I don’t think we were a match, but it was a blast having such a unique evening with a total stranger.”