The Pros and Cons of the Types of Guys You'll Date

This article is composed of entirely true accounts of very real, very...insightful encounters with a few of the types of guys you might date in your lifetime. If you’ve dated them, then you already know…

The High School Sweetheart

Who he is: He’s your first real relationship, prom date, and someone who will always have a little piece of your heart. There is so much history there and the two of you have spent irreplaceable time growing up together.

Pros: No matter where you end up in life, you’ll always share the same hometown. You know the same people, spent your childhoods in the same places and he doesn’t need directions to your parents’ house. You’ve become so comfortable with him and his family that when you show up to his house, his parents are happy to see you and you’re way past that “this is awkward, I’m dating your son” phase. You’ve got a lot of history together, and the two of you have been through it all and know so much about each other. You really do have so many memories and experiences to look back and smile on. Bottom line, it just feels easy and comfortable to be with him. And not to mention, how cute would it be to show your kids pictures of their Mommy and Daddy at prom in 2013?

Cons: There’s always going to be history there, and the two of you broke up for a reason. No matter how much you’ve each grown up, sometimes it can never be enough for one or both of you to completely come to terms with the hurt or disappointment that’s associated with the relationship you had in high school. And even if you can get over this, sometimes, going back to that relationship can feel a lot like settling. It’s easy, and it’s comfortable, but maybe it’s too comfortable. It might be painstakingly easy to fast forward 30 years from now and imagine having nothing left to talk about. You deserve to feel like a little kid in a candy store, not like your relationship has been dragging on and on for years already, and you’re only in your twenties.

The Rom-Com

Who he is: He is, by far, the most romantic and thoughtful guy you’ve ever met, and you’re constantly impressed with him. We call him the Rom-Com because he learned everything he knows from watching romantic comedy movies with his sisters, and he’s the one who insisted, “you just have to watch The Notebook”, when you told him you’d never seen it.

Pros: He’s one of the only guys you’ll meet that actually understands the meaning of chivalry. He'll cook you dinner, open the car door for you, and bring you flowers for no reason. He’s respectful, generous and kind, and your parents will love him. He’s family oriented and he thinks it’s important that you get to know his family too, because he swears, “they’ll love you”. He genuinely makes you feel like you’re the most special girl in the world and that he’s lucky to spend even a moment of his time with you. Even after it’s over, sometimes you still imagine it working out in the future because he’s total hubby material. Sounds perfect right?

Cons: You’re not really sure if he realizes that life actually isn’t a romantic comedy. Sometimes it gets hard to believe the romantic gestures and over the top compliments are genuine after however many months. You start to think maybe he’s too nice and a little predictable, and maybe even a little boring. You want to be challenged or at least surprised, so you end up picking fights, and eventually the climax of the romantic comedy occurs with the big, blow up argument and dramatic ultimatums. And like I said, rom-coms are not realistic, and unfortunately, it usually doesn’t end happily ever after.

The “What Were You Thinking?”

This is the one that you, and everybody else, saw coming a mile away. He’s a complete jerk with a terrible track record. Naturally, you ignore all of this because you simply cannot ignore his overwhelming attractiveness and incredible charm.

Pros: Well first of all, we have to address his undeniable good looks. I’m talking sparkling blue eyes, soft brown hair, tanned broad shoulders and a great butt (just sayin'). You don’t just put up with a total jerk unless you at least really, really enjoy looking at him. But then things start to get a little more serious, and you actually start to realize that you’re never bored with this guy. You like how he’s blunt, honest and intelligently opinionated and you slowly uncover that he actually had goals for his life. He’s spontaneous and charming, and he’s always making you laugh, even if it’s at your own expense. He drives you absolutely crazy, which, you can’t really figure out if it’s a good or a bad thing, but it’s the most you’ve actually felt in a while. Most importantly, what you like most is that he challenges you. He makes you rethink things, take a stance on what you believe in and fight for it.

Cons: Eventually, you’ll rethink him, and take a stance on the fact that he’s just a total jerk. He’s selfish, crude and thinks he’s completely invincible, constantly putting himself and others in danger without a thought. He constantly talks about other girls in his past (or present) and never fails to mention how he thinks “you would be 10x hotter if you went to the gym”. He really doesn’t care about your feelings, but the worst part is that he’ll act like he does and he’ll offer handfuls of empty promises. He’s totally not ready for commitment, or even just an exclusive “thing”, and he’ll disappear from your life without more than a late night text. But watch out, because he’ll probably show up 2 months later acting like nothing ever happened.

The One That Got Away

We’ve all got one.

Pros: Well, pretty much everything. He’s the guy you kind of think is totally out of your league. Your relationship progresses slowly but surely, building every day. You stay up late talking about politics, religion, aspirations and family, and you just seem to be on the same page about what you think is important in life. He makes it a point to get to know your family and the things that are important to you become important to him. Soon, picturing a future with him is as easy and as effortless as blinking, and it becomes hard to imagine life 30 years from now any other way.

Cons: Sometimes, we’re not really sure how exactly what happened, and maybe, at the time, you just didn't realize the impact if would have on you. It seems like things are maybe unfinished and you’re lacking closure or still wondering about all the "what-ifs". But I guess I'd have to say that the biggest con about him is just the simple fact that somehow, he got away.

In the wonderful world of dating, all I have to say now is good luck.