I’ve been thinking a lot about my dating history lately, and I’m honestly tired of feeling bitter and cynical. It’s like every relationship I’ve had ends up with me getting hurt, and I’m starting to wonder if it’s ever going to change.
Let me take you back. My first girlfriend was in high school, junior year heading into senior year. We were in the music program together, and after months of her gushing over some other guy and asking me for advice, she suddenly had a crush on me. I was so stoked that someone actually liked me that I ignored the red flags. She had dated a ton of guys in the band—the stereotypical band BLEEP, if you will. It was a fling for her, a first for me. Then I moved to a new school for senior year, and we just drifted apart. Mutual silence. She lost interest way before I did.
Second girlfriend? Felt like pity. She approached me, had a crush, and I couldn’t say no because I’m a nice guy. But she was so into herself, sheltered, and just used me as a trophy. Ended it after one of her hissy fits.
Third was introduced by the second. We clicked somehow, and then I found out she was literally crazy—thought she had past lives, thought she was a cat, saw things, self-mutilated, ran into the woods at night because “spirits called.” She cheated on me with my best friend. I forgave her once, but the second time? Done. That’s when I started hating high school drama.
Fourth was a friend of the third. She admitted she had a crush, and I agreed. She was cool but went through a copycat phase, mimicking my third ex’s crazy behavior. I was about to break up when a friend introduced me to someone online. That turned into the fifth girlfriend, but it started badly—I kissed her while still with the fourth. I told the fourth the truth, and we broke up. The fifth and I were happy for a month before I left for basic training. She broke up with me by letter right before Christmas, and I later found out she started dating an old friend. Whether she cheated or not, I don’t know.
Three years passed, and I tried again—met a girl online. We clicked, webcamed daily, I was head over heels. I blew off college, didn’t sleep, neglected my job. After six months, I flew to see her. I imagined the perfect reunion, but when I got there, she barely hugged me. We stayed at her place (parents were gone), and she threw a party. I woke up to her having sex with some guy she just met. I left at 4 AM, walked to a friend’s house, and flew back shattered.
A year later, one of my best friend’s sisters told me she wanted to date me. She was 17, I was 20. I said no, but she insisted on friends-with-benefits. I gave in, and after she lost her virginity to me, she said I was too old for her—exactly what I warned about. I felt used. Then I heard she did stuff with two guys at once days later. I was furious—not just at being used, but at her recklessness. I talked to her dad to try to protect her, but of course she saw it as betrayal. We don’t talk anymore.
Now I can’t look at a girl without thinking she’ll use me or hurt me. I’ve always treated my exes well—sacrificed, gave gifts, was gentle—and I always end up with the short end. I don’t want to feel this way, but I’m scared to try again. I want someone special, but I’m terrified of hurting her or being hurt. What do I do?