OyChicago blog

Valentine's Day is more than a month away, but I am hating on love a little early this year.

Love songs are like audible reminders of lovers past. If I hear a song that frequented the radio waves while I was dating a certain guy, it sticks. I will always think of him years later when I hear that song. Just like Selena Gomez's Love You Like a Love Song, it's painfully hard to forget.

For instance, I can't listen to Regina Spektor's Samson or Fidelity without thinking of an ex I dated one summer during college. Dave Matthew's Band's Crush will always make me think of my high school crush (no pun intended). Often, I hear Adele's Someone Like You come on my car radio during my evening commute and I want to cry a little bit—but let's face it, we all find someone to identify with that song—that's why her "crib" is now filled with Grammy's.

If only our senses and memory triggers were that strong when meeting and assessing new potential mates. I knew I had the topic for my next Oy article when I found myself re-dating.

During lulls in my dating calendar, I return back to the online dating world, only to be more disappointed and horrified by what I find there. A recent encounter involved a guy who shoots video for some of the major sports teams in Chicago. He seemed interesting enough, although I have little-to-no interaction with football, hockey and the like. Friends and family annually have to inform me when my alma mater is doing well or entering into a bowl. Someone mentions a "sugar bowl" and my brain trails to where I can find my next chocolate fix. After conversing with him via the site over several weeks, he sent me his phone number. I entered the number into my phone, only to find I'd already programmed him in my phone—years ago.

Somewhere between laughter and panic, I recalled the Season 9 episode of Friends, in which Joey enters his date's apartment, only to find he's already been there. He's dumbfounded that both he and his date can be so slutty as not to remember each other, until Joey's date's roommate walks in and he realizes he had previously dated her instead.

While my proverbial "little black book" isn't as full as Friends character Joey Tribbiani's, I still managed to get picked up by the same guy twice without realizing it. I code people in my cell phone by how I meet them, and I had coded this sports guy as "Camera Man." He apparently had left so deep an impression the first time I met him, that I didn't actually put his name in my phone. I must have entered him in my phone for the sole purpose of screening him. I did, however, recollect how we'd met. He and I worked in the same office building a few years back, and he worked for a different division of our company. With no prior introductions, he'd cornered me one day in the parking lot and asked for my phone number. I remembered thinking at the time that he was very awkward and I just wanted to escape to my car. Thankfully, he never followed up after his bold number exchange—until now.

I couldn't actually meet this guy face-to-face without confronting the back story. Present day" Camera Man", meanwhile, kept texting me to meet for a first date at odd hours, requesting, for instance, that we grab midnight drinks at Big City Tap. This should have been my second red flag. I tried to give him the benefit of the doubt and considered that he might work odd-hour shifts with his line of work. There are no excuses, however, for proposing Big City Tap. Generally, making excuses for guys' bad behavior is not productive or advised.

The week we arranged to meet, I finally texted him my hypothesis of how we'd already met. I was correct; he was shocked. He appeared not to be scheming. In fact, he seemed happily surprised. Thus, I agreed to go through with an actual date.

We met for an early evening drink. Half the night consisted of civil getting-to-know-you conversation over beers. The second half of the night, I played defense to his offensive pawing (see, I can use sports terms!) and late-night invitations. I felt like I was on a date with a horny 15-year-old. Camera Man was no Joey Tribbiani; he wasn't slick enough. Rather, he was a forever-awkward (and apparently forgetful) doof, fueled by alcohol and false confidence.

Lessons learned? I should code my phone better and follow my initial instincts. It saddened me that for a brief moment, I romanticized this guy before meeting him. I thought our scenario could be like the movies: We meet once, but the timing is not right; we meet again, and it's magic. I think I've been watching too many romantic comedies on television. Sleepless in Seattle and Love Actually can wreck a girl for real-life romances for years.

Some re-encounters with those we've met in the past are eye-opening in a good way. I've run into old friends and people I've dated or been interested in and seen them with fresh eyes, as we're both in different places in our lives. Revisiting those old romances or "wonder-if's" can be amazing and/or heart-breaking.

Online dating has the tendency to magnify all of the problems of "in real life" (IRL) dating and even exacerbates them. When two people meet in person for the first time, the process of getting to know each other is a tango between two people showing the best versions of themselves. In online dating, you get all of that first date info and best-self impression fluff out of the way before you even meet. Often when you actually then meet each other IRL, the crazy seems to come out more quickly. As with shopping online, expectations are inflated before contact. It's like picking the toy out of the cereal box and realizing it's half the size and made out of a really cheap plastic. (P.S. Guys lie constantly about their height on their profiles. We never know whether to wear heels or flats, because who knows what's going to walk through that door?)

In all fairness, my perspective is heavily informed by the female experience, because I mostly talk with women about their online dating stories. I know guys who have their horror stories about us too. However, it seems some men, in particular, use these sites to get laid, trade up, mess around and altogether inflate their egos. For some, it's a game, and we, ladies, weren't given the playbook.

The truth is, as much as I love to bash Internet dating sites, navigating getting to know someone you initially met in person can be equally puzzling and demoralizing. Everyone has skeletons in their closet. Through dating, we only get to peek at them, a bone at a time.

As some Oy readers might recall, my Valentine's Day tribute last year was also centered on a nightmare online dating experience. It grieves me that this year I had yet another tale to tell. Last year, I categorically delved in the creepers trolling the dating sites. I won't do that here again.

However, I will recall my aforementioned thesis that amnesia, perseverance and optimism are needed in this crazy dating world. In my case, a little less amnesia might save me some time.