A dating dare

The year was 2005. I was coming up on the end of my first year of college. And what a year it had been! I started the year out homesick only to do a 180 and find myself not wanting to head home for the summer. After a short-lived long-distance relationship and a failed attempt at dating a fellow freshman, I was going into a long summer in the suburbs very, very single. And my good friend Polina was facing a very similar situation, just home to her was a bit further away in Korea. So she had a genius plan! Whoever could get a boyfriend for the summer (summer fling, anyone) would win the bet. I think it was something silly like 5 dollars and/or bragging rights. But it lit a fire under my butt.

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And that was a fire I very much needed. A push off a long-term obsessively ridiculous love for someone I had never met. Ask me another time about that one. But what happened next wasn’t exactly what I expected. I signed up for a free dating site (I was a poor college student who had just finally picked up a summer job!) and within days was inundated with messages from nearly every eligible man near Chicago (and Bloomington???). After carefully weeding out the very noticeable weirdos, I settled on meeting three guys who seemed the most interesting (or least creepy however you’d like to see it).

I liked the first guy. Actually, almost so much that I nearly considered calling off the other two. But there was two things that kinda threw me off about him that I noticed on the first date. And while they weren’t deal-breakers, I didn’t want to torture myself over the long, hot summer with someone I’d have to settle for just to win a bet. So I met the other two guys.

The second guy was awful. The red flags were burning from the beginning, but by the time I decided to call off the date it was too late. So I actually had my guy friend join us on our date, making it more of a casual hangout session. He still tried to kiss me at the end of the night, which didn’t happen. The third guy caught my eye, and on the second date I fell in love with… his mom. Fast forward, I cut things off with the first guy and third guy asks me to be his girlfriend halfway through summer. I win the dare, I win the bragging rights, and I get to hang out with a pretty stellar guy.

His family is great, and actually one of the first examples I witness firsthand where step families get along and mesh well together. He has a step-brother in California, an older brother his mom had during her first marriage. Her first husband moved on and had another family of his own, and all of them are friends. So original marriage, divorced but remained friends. I didn’t know this level of forgiveness and friendship existed. And it was beautiful.

I liked the guy too, but I think a part of me just grinned and bared it for the gloating rights. I also expected him to dump me and move on once we turned into a long distance relationship. The main reason for that thought was that the only other girlfriend he had was someone who lived a few blocks from him. I was already pushing it being about 25 minutes away, I doubted he would survive with me being 2.5 hours away. But once back at school, he proved me wrong. We worked something out and ended up seeing each other every 3 weeks.

What was supposed to be a summer fling, ended up lasting 2 years and 4 months, y’all. My point is, never label something until you know all the details. I learned the hard way to not just write someone off as a fling. Actually, that might be why to this day I still try to imagine myself being with whoever I’m dating for much longer than just that moment. It tends to get me in trouble. Thanks to the summer dating dare, I now try to see if Mr. Joe could be Mr. Brice (obviously he would take my name bc it is superior lol).

This has bitten me in the butt a few times, most noticeably recently when my mind was about 5 million light-years ahead imagining things actually working out with someone only to have him not even give me a chance and choose someone else. So maybe I have to work on balance. Not just write someone off as a fling but also stop imagining myself walking down the aisle in a white dress with them. At least make it a cool color!

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