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My Experience With Online Dating

By Kevin Gottlieb

“Oh, this is a date? I just use the site as a way to meet friendly new people. I’m not looking to date anyone right now… I’m still sleeping with my ex,” The Backslider said as I slowly began losing faith in online dating.

I want preface this article by saying that I’m a pretty traditional guy, and I don’t date anyone that I can’t see a future with. “Dating around” isn’t really my thing, let alone meeting a stranger on the internet, but I decided to give online dating a try in late 2011, just to see if anything could come from it. This is my story.

Loyola University Chicago has a girl-to-guy ratio of almost 2-1, but for some reason, finding someone who was “girlfriend material” was proving difficult. I knew there had to be some great girls here, but I wasn’t looking in the right places.

For example, I met a girl at The Pumping Company. After some flirting and dancing she asked me to come back to her boyfriend’s house. Who does that?

I had serious reservations about online dating myself, but I’m sharing my experience with the website DateMySchool to show that online dating doesn’t have to be like the creepy AOL chatrooms of the 90s. DateMySchool was easy to use, anonymous, and effective.

Armed with a witty alias (ChivalryIsNotDead) and a profile picture that was iconically me (playing golf in a Blackhawks windbreaker and a Cubs hat) I started looking at profiles.

Zachary Hayworth is part of DateMySchool’s operations team. He said “we combat all of the major reasons why people DON’T want to join a dating site.  When it comes to other websites, people don’t feel safe.  We are safer than any other dating site and online social platform in the world.  We verify everyone.”

There seems to be a stigma of weirdness attached to the idea of online dating, despite the fact that 40 million Americans use dating sites according to America’s Bride Wedding Magazine. I decided to try it anyway.

Because the ads for DateMySchool were small, I feared that the site would have a very small user population that would get even smaller once I entered age and location parameters. I was pleasantly surprised.

“Today, DateMySchool has nearly 200,000 members and is adding hundreds, even thousands of new users every single day… [We are] currently open to all 2,400+ accredited 2-year and 4-year colleges and universities,” Hayworth said.

I liked that it was anonymous and secure. The site never asked for my name, and it allowed me to control the demographics of the people who were allowed to see me.

“DateMySchool is completely anonymous.  Your roommate, your friends and the kid next to you in class will NEVER know you are using us.  We don’t ask for anyone’s full name, zip code or any other personal information, either,” Hayworth said.

Students can pay for a more specific search capability on the site, but I chose to use the free version of DateMySchool. The choice limited me to searching in the Chicago area and I couldn’t search by body type or hair color.

I was still able to filter searches by things that would tell me about the girls’ personalities like religion and college major. I never searched by major, but I did want to date a girl who held the same Christian values as mine.

“College students want to meet other college students with the same academic/professional interests and goals.  We give them all of this and more by being exclusive to the academic world,” Hayworth said.

One thing about online dating that is very different from real dating is the honesty. After my first date with Lemon Law Girl, we agreed at the end of the date that we were nice people, but according to her  “there was just zero chemistry.”

Being a blunt person, I appreciated the honesty. I even agreed with her about our mutual lack of interest, but that didn’t mean that  I was really buying into the idea of meeting strangers from the internet either.

Then I met The Backslider. She was also very honest, but in a different way.

“I’m still sleeping with my ex,” she said.


I thought this was weird, given the site’s name, but she said that on her other dating sites (such as OkCupid and Plenty of Fish), she had met “a lot of people who were just looking for friends.”

The people who manage DateMySchool acknowledge that some people don’t use it for romance.

“Some users simply want to meet new people on campus.  Others want to network with students from other schools, meet new people from surrounding universities, or find a study buddy, while other users are looking for romantic relationships,” Hayworth said.

I went on a few coffee dates with The Phantom. I’m not sure what happened here. We had fun together, but after (what ended up being) our last date, I saw her walking around campus while holding another guys hand.

I’m not sure what happened here, but she seemed happy and it ended up working out for me eventually.

The Vegetarian did not like me. We met for lunch at Pillars and tried desperately to make conversation for an hour, but most of the talking was about foods that we didn’t like.

Vegetarians are just as likely to be my friends as any other people, but I wouldn’t want to date a vegetarian. I’m a picky eater, but I love chicken and beef, so between my choosiness and someone else’s different choosiness, there would be virtually nothing left that we both liked to eat together. Oh well.

I was going to delete my account because I was becoming very frustrated, but when I logged on for what I thought would be my last time I saw a picture of the girl who is now my girlfriend. I clicked into her profile and it looked promising. She was a Christian, loved reading, and her secondary photos included one of her making a s’more, one of my favorite desserts.

We exchanged “looks” (you are notified when someone views your profile) for about a week, then I messaged her. We talked about how we root for rival baseball teams, how we both watch How I Met Your Mother, and how we thought it was ironic to hold such traditional values and meet in such an untraditional way.

Eventually we met in person, went on a few dates, and a year later, we’re still “going steady.”

I haven’t been on DateMySchool in over a year, but looking back, I think it’s just as valid as normal dating. Some relationships work romantically, but the majority of them don’t.

Online dating makes finding willing date companions easier, but even if you spend weeks instant messaging a person online, you can’t truly know them until you meet them face-to-face and hear their voice.

Dating is hard, online and offline. People rarely spend the rest of their lives with the first person they ever date, whether they meet online or off.

Whether you decide to date online, offline, or both, remember what country singer Brad Paisley said about the risks of new romance, “if love was a plane, nobody would get on.”

Would you ever try online dating? Take the poll and comment below!


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