Dating apps have given us unprecedented access to every nut job, borderline sociopath, and bunny boiler in Chicago, and having a nightmarish experience has become some sort of twisted rite of passage. We asked a handful of Chicagoans to share their worst online dating stories, and we were not disappointed.
“I’d matched with this guy on Tinder and we quickly discovered that we had a bunch of acquaintances in common, including some high school classmates and old coworkers.
“I miss you’s” were reserved in my mind for friends and lovers who had seen me through at least a round of emotional highs and lows.
And that evening when I got home, we exchanged messages of excitement and desire to see each other again as soon as possible. When I left his house that night, at my own insistence, he told me how he couldn’t wait to see me again, to take me out for dinner to his favorite restaurant, and to go on more dates with me after that. Here was a man who I shared a strong chemistry with, found to be incredibly attractive, impressed me with his professional work and personal aspirations, kept me laughing and interested, exhibited a real openness and sincere interest in me, and was thus far kind, attentive, and intelligent.
The next evening we went to a bar in our shared neighborhood where we asked each other about work and family and hometowns and hobbies, and he kissed me with full soft lips on my mouth and neck. The next day I left New York to return home for the holidays.
Spending too much time on Tinder, Bumble, or Ok Cupid will make any sane person yearn for simpler times.
You know, like when singles met potential mates at corn husking bees or whatever.
He wasn't supposed to stay the night, but he lived 45 minutes away, it had snowed earlier, and I lived in a very rural area with a lot of hills and curves.
So he decided he was going to stay that night instead of driving home.After chatting for a couple of weeks, we decided to meet up at a bar.Everything was going really well, until he got a few drinks in him and he began telling me obviously fake or exaggerated stories about how wealthy and successful he is, which was a huge turnoff.On a first date when I was a freshman in college, we were going to go to the reservoir for the afternoon on a beautiful Indian Summer day.First, we had to "get some cash." He took me to a blood bank to donate plasma!It began as a fun flitting in my chest, smile and daydream-inducing, goofily saccharine the way most beginnings of good things are. A combination of polite questions, witty banter, and explicit flirtation (enhanced with images) kept us both delightfully entertained and engaged.