02/24/23

recently I have been coaxed/nudged/forcefully pushed back into the dating game by my friends and family (see: The Zoo blog post for a quick recap of a recent dating escapade I participated in)

as I’ve written about before, I tend to stay single for long periods of time between relationships. I’ve never really been a casual dater, so that has been something I’m trying to do as a way to stay busy and get outside of my comfort zone. a quick breakdown of my entire dating history:

• my very first boyfriend, we dated for two months (see: The Valentine for that story in all its glory), we broke up when I was a sophomore in high school
  • [insert two year break here, didn’t date again until I was a senior in high school]
• my first “real” boyfriend, we dated for two and a half years, we broke up when I was a sophomore in college
  • [insert two+ year break here, didn’t date from the end of sophomore year of college until the summer before law school]
• an engineer I went on two dates with before law school who lived in midland and broke things off bc he said me being in law school would be too hard for him????
  • [insert one year break here, law school devoured all my time and energy]
• a different engineer who I also went on two dates with, he had moved back home bc of the pandemic but planned to go back to Chicago at some point. nice guy but our senses of humor did not click and I thought he was so boring – he tried to kiss me after our second date and I definitely panicked and swerved away
• my next boyfriend, we dated for a year and then broke up my final semester of law school
  • [insert one year break here]
• a med student, we went out once and talked about our shared love of Taylor Swift
  • [brief hiatus for the 2022 holiday season, I did not want to be roped into holiday parties or end up meeting people who were only in town briefly to see family]
• an attorney, so funny and had a great time but definitely think we clicked more as friends
• a guy in finance, we went to the dog park and sparks were just … not there
• a restaurant manager, very funny and cute, hope to see again but his schedule kind of sucks so we will see

and that’s everyone! literally nine boys LMAO. so the fact that in the past month I’ve gone out with three guys with two more dates from additional boys potentially in the works is saying a lot for me. if anyone wants to share any dating wisdom I am all ears.

things I am grateful for: excuses to dress up and look cute; benefiting from outdated gender roles that usually means the guy buys my drink; and the knowledge that it’s not that serious and it’s okay to just have fun.