I Dated My Teenage Crush As An Adult And Here’s What Happened

I Dated My Teenage Crush As An Adult And Here’s What Happened

He wasn’t just my crush, he was everyone’s crush. People tuned in to see him on a local TV show every week. He was cute, funny, with soulful brown eyes. If someone had told me that I was going to meet and date this guy in the future, I would’ve thought they were on hard drugs, but it happened and it was… interesting.

  1. I used to skip school to watch him. I’d miss school so that I could watch his show on TV. It was a music talent show and he was one of the tutors to the contestants. Since it was a reality TV show, I got to see the guy having normal conversations with the contestants so it felt like I was in the room with them.
  2. I got caught up in a daydream. I couldn’t help but daydream about this guy all the time. I wished I had some sort of musical talent so that I could’ve entered the show and met him. God, imagine spending so much time with him behind the scenes of the show! I would’ve died.
  3. I “liked” him on Facebook. A few years later, I “liked” his Facebook page and started following him to stay updated on his news, but as the years went by, I totally forgot about it/him. He was a local celebrity who updated his fans and followers, but that was it.
  4. Then one day, I got a message from him. It was so weird—I logged onto Facebook and saw a message from him. I assumed it was a message for all his followers or that it was spam, but it was neither. He wrote to tell me that he’d been going through his followers when he saw me and wanted to chat to me because I seemed like an interesting person.
  5. I was shocked! I couldn’t believe he’d sent me a personal message, but still, I knew it didn’t mean anything. He was just being friendly or something. We started chatting a bit and found out we had loads in common. He was really fun to talk to. Then he asked for my phone number and things started moving ahead.
  6. I needed to pinch myself. Our phone conversations were filled with laughter and we shared stories about what it was like being in creative careers. A few times during the phone calls, I was just like, “WTF? Is this really happening?” Then, after a few conversations, he asked me out on a date. 
  7. That Katy Perry song was about me. It was so freaky that my teenage crush was asking me out on an actual date! I felt like that “Teenage Dream” song by Katy Perry was totally about me because this guy was making me feel like a teenager again. I was so excited to meet him. Who knows? Maybe we’d fall in love and he’d write songs about me!
  8. Wait, can we do that again? So we met for a morning coffee in the middle of the week when we both could get out of the office and when we hugged, the first thing I noticed was that I was much taller than him in heels. Hmm, okay, no biggie. I settled into the date and we had a great time. We laughed, we chatted, and the time flew. The only problem was that I felt no spark. Seriously. I thought it was just a case of nerves, but there was literally nothing.
  9. I couldn’t believe my bad luck. This was really unfair. I mean, there I was sitting opposite a guy I’d been crushing on for years and I felt nothing for him. Reality hit home that how someone is on TV isn’t always what they’re going to be like in real life. Also, I’d really crushed on this guy almost 10 years ago. Maybe my taste in men had changed and I hadn’t realized it!
  10. I really tried because I wanted it to happen. I so wanted this to happen for us. I really tried to focus on the great connection we had and how entertaining the guy was. Plus, when he belted out a song, it sounded so good! Still, the more I looked at him, the more I realized that I didn’t feel a physical attraction. Just because I’d been crushing on him hard from a distance, it certainly meant nothing and wasn’t a guarantee of a hot romance in real life. Ugh.
  11. The worst was yet to come. We could’ve just gone our separate ways with no hard feelings as I planned to do, but then after the date, he sent me a message telling me how much fun he’d had and he asked me out again. Oh man, this complicated things.
  12. I thought maybe we could be friends. I didn’t see relationship potential with this guy but I enjoyed our conversations. However, I knew it wasn’t fair to lead him on. I had to tell him that I didn’t feel anything but I asked if we could still be friends.
  13. He felt differently. He made it clear that he really wanted to go on another date with me and he wasn’t looking for new friends. Uh, really? This had to be the worst thing ever. I crush on a guy for years then get to date him and he actually likes me but I don’t want him? Talk about having rotten luck.
  14. He blocked me. We decided it would be best to go our separate ways and not stay in touch. A few hours after our last conversation, I logged into Facebook and saw him complaining about women and how hard it was to find one. Then he deleted and blocked me. Ouch! So much for “no hard feelings.”
  15. I confirmed my decision. I don’t know why I felt the need to look through his Facebook profile after we dated, but I guess in some way I wanted to see that I hadn’t made a mistake by rejecting this guy. When I looked through his photos, he looked cool but I felt no attraction. I’d made the right choice. When I looked through posts on his wall, I found something really interesting.
  16. He was a woman magnet. There were women talking about how much they’d love to date this guy and others who were singing his praises. Geez. Clearly he was used to the attention but just because I’d been keen to date him didn’t mean I was a done deal. I’m glad things didn’t work out. Being with someone who’s so used to female attention is probably not the best thing for a relationship. Plus, I hate to say it, but I really want to wear high heels and not be able to see over my partner’s head.
Jessica Blake is a writer who loves good books and good men, and realizes how difficult it is to find both.