A Comprehensive List Of Every Guy I’ve Dated And What I Learned From The Relationship

Note: I use the term “dated” loosely and for the sake of clarity. These are more or less in chronological order.

Nathan L.
Kindergarten. I learned that contrary to the advice in magazines, it’s fine to be smarter than your boyfriend. If he’s a quality guy, he’ll appreciate that you’re able to teach him things and help him understand the world.

Brandon A.
Middle school/High school. I learned that it’s possible for someone to treat you like absolute shit and still walk away from the situation feeling like they’re the good guy and you’re the villain. I learned that some men will ignore your boundaries and won’t respect the word “no”. I learned the legal process for filing a sexual assault claim, and I learned that it won’t actually help. 

Austin U.
High school/College. I learned that it’s a waste of time for all parties involved to date someone just for the sake of being in a relationship. You might be able to pin a guy down into being your boyfriend, but if he doesn’t actually know you or care about you then you’re not going to get that Boyfriend Treatment you’ve been looking for.

Eric D.
College/Post-college. I learned to trust my instincts when a guy was giving me mixed signals. I learned to play it cool and let the other person make the first move instead of making myself vulnerable. I learned that it’s possible to do everything right and still have a situation blow up in your face, and the only thing you can do to retain a little dignity is walk away. I learned that someone can be unfailingly polite and still incredibly cruel.

Will N.
College/Post-college. I learned to stop going after men just because I thought they were attainable. I learned that sleeping with someone doesn’t automatically guarantee that you’re in a relationship. I learned that a legitimately mutual breakup still sucks if you’re not the person who brought it up first.

Anthony G.
Post-college. I learned that it’s actually possible for a relationship to be casual and uncomplicated.

Micah F.
Post-college. I learned that it’s actually possible for a relationship to be casual and still very complicated. I learned that you should always respect Girl Code and make sure that you’re not going to get into a fistfight for going on a date with someone’s ex-boyfriend. I learned that if you do get into a fistfight for going on a date with someone’s ex-boyfriend, you should immediately seek to retain sole custody of the video that your toxic BFF takes of the incident. I learned not to date within your friend group, not even the extended friend group.

Phil S.
Post-college. I learned that having a one night stand isn’t the sad and pathetic thing that Sex and the City had led me to believe, nor is it the empowering and feminist thing that Sex and the City had led me to believe. It’s just rolling the dice on a guy, being pleasantly surprised when you get to his apartment and he owns the complete DVD collection of Frasier, and being only mildly offended when he never calls you again afterwards.

David ?
Post-college. I learned not to get trapped in a situation where you’re dependent on a man you don’t know very well.

Chris C.
Post-college. I learned that you can’t fix someone. I learned that being shitty and manipulative isn’t more acceptable when the person genuinely doesn’t realize they’re doing it. I learned that you can decide something you previously put up with isn’t okay with you anymore. I learned that you don’t have to stay in a bad relationship just because you’re already in it.

Matt S.
Post-college. I learned that sometimes two people are both perfectly lovely, and they just won’t click with each other.

Peter B.
Post-college. I learned that it’s totally okay to lose interest in a guy for no real reason, or for a completely superficial reason that you have to pretend was “just one of those things” because telling him the actual reason would make you sound like a shallow bitch. I learned that not every potential relationship is worth putting in the initial legwork, especially if it requires you to reverse course on a personal dealbreaker for a guy that so far you only sort of like.

Caleb R.
Post-college. I learned to trust that funny feeling in the pit of my stomach. I learned that if you have a suspicion that a guy is lying to you, or using you, or two-timing you, the most likely reason for that feeling is because he IS lying to you, using you, and/or two-timing you. I learned that if you ever find yourself competing with another girl for your man, you only lose if you decide to keep competing. I learned that you can’t make someone else feel remorse for their bad actions. I learned that self-reflection is the only tool we have in healing from past traumas.

Ryan K.
Post-college. I learned not to bring my prior relationship’s baggage into a new relationship. I learned to just speak my mind instead of playing games. I learned to call a guy out on his bullshit the moment he starts trying to pull one over on you. I learned that if a guy is cagey about people knowing that you’re together, it’s because there’s something wrong with him, not you.

Kevin M.
Post-college. I learned that you don’t win any prizes for trying to be nice. I learned that when you’re the only girl nice enough to give a certain guy a chance, you should stop and ask yourself why no one else is making the same mistake. I learned that the most docile, unassuming, throw-him-a-bone-he’s-a-nice-guy type of dude can still be a MASSIVE creep.

Jim B.
Post-college. I learned that going after someone who you wouldn’t normally like might expand your horizons a little bit, but you might also just wind up with someone that you still don’t actually like.

Max S.
Current. I’m learning that most of the Life Lessons you think you’re collecting from previous relationships are just a catalogue of things that were wrong with a particular guy, or things that were wrong with you at a particular point in your life. When you actually meet someone worth a damn, you don’t feel like you’re making an entry into your little black book. You feel like you’re closing the book and starting the only chapter that actually matters. 


Brandon G.
Elementary school. Don’t take relationships too seriously, no one really knows what they’re doing.

Kasey S.
Elementary school/middle school/high school. Waiting for the right moment to make a move is just a surefire guarantee that you’re going to let every opportunity slip by you.

Jake T.
Middle school/high school. If you don’t know someone well enough to sustain a three-minute conversation with them, you definitely don’t know them well enough to justifiably have a crush on them.

Nick D.
Middle school. Just ask the guy out. Life is too short to waste time.

Casey G.
High school. You’re allowed to have a crush on a girl. Anyone who makes you feel weird about it is an asshole.

Robert R.
High school/college. I rarely say this about any of my life experiences, but I learned absolutely goddamn NOTHING from this one.

Jeremy W.
College. Any boy prettier than you are is going to break your heart.

Author: Bryanna Doe

Author, storyteller, comedian, songwriter.

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