LT's Adventures in Men: a tale of awkwardness and confusion

  1. The middle school crush
    He borrowed a pencil from me. He never returned it....because he lost it. But he got me a replacement pencil. I was convinced it was true love. 😍
  2. The first person to ask me out
    We met at Mathletes, where he asked to borrow a pencil. He was a junior, with an throng of female freshmen admirers. I was a freshman, but not one such admirer. Let's just say that when he presented me with a rose on Valentine's Day, it made for awkward conversation. 😟
  3. The first real crush
    It began when he comforted me after a particularly brutal math exam. It lasted for a solid year, and then on-off for another two. There were Facebook marriages and engagements. There were coy comments from friends. Later found out he's gay. 😩
  4. The first kiss
    I had braces my freshman year of college. He was drunk. He kissed me on the couch at a house party, and then texted me the following day to apologize. 🙊
  5. The disillusioned crush
    I thought he was fun and easy to talk to. Then I saw him kiss a girl he knew to be taken, and then he cried to me about it. That spark quickly died. 😵
  6. The pretty one
    He looked like he walked out of a Ralph Lauren ad. I admired him from afar. 😎
  7. The awkward one, pt. 1
    He also had braces, but didn't know who Frank Sinatra was. I was bad at turning people down. We saw each other consistently for the next three years on the college journal. (He was also in the same section as the boy below, which messed with my brain for a whole semester.) 😬
  8. The troublemaker
    We wrote for the same section in college on international affairs journal. I confessed to him that I liked him. He liked someone else. Cue the next two years where we still work together, banter with each other, and (according to various eyewitnesses also in the journal) had lots of sexual tension. He asked me out senior year, and I turned him down. I still wonder what our hypothetical relationship would look like, before realizing it would have gone down in flames. 😌
  9. The first boyfriend
    He was lovely and gregarious and courteous to my parents. But he also made some racially insensitive comments at me and wasn't the most supportive while I studied for the LSAT. My one regret will always be not leaving him sooner. 😑
  10. The longtime friend
    There are moments when I think he's decent. He's good-looking, tall, fit, charismatic, easy to talk to, and generous. But he's also politically apathetic, thinks I'm too opinionated, and likes "docile" girlfriends. 🙄
  11. The instructor
    Thick hair with specks of gray. Always had the answers. Charming smile. Made a pass at me, which thrilled me. Later turned out to be a braggart....with a girlfriend. 😒
  12. The awkward one, pt. 2
    This time, we actually dated. We dated until his insecurities and snarky humor became too much. But I can't say anything bad about him, because he deserves better. My not regretting the breakup doesn't mean I don't care or I dislike him. Quite the opposite. 🙁
  13. The forward one
    We met at a friend's birthday party. He chatted me up and asked me for my number. Never texted. Saw each other two months later, and he approached me to give me a hug. Chatted all night. Still no text. He was cute (the first time I preferred someone to have facial hair, too). I give up. 😡
  14. The brilliant one
    We were in the same classes during 1L but only talked after 1L was done. But I still knew he was insanely smart. And painstakingly nice. During September of 2L, he asked how long I've been broken up with my ex. We go out 3x (dinner, movie at my place, movie at a theater); he calls me to ask how my day is; he walks me home from the subway; he wants to hold my hand and kiss me. Then on Election Day, he decides he's not feeling it. But then showed up at my birthday party a month later. 🤔