EDITOR’S NOTE: Jared Freid (Twitter: @Jtrain56 / Instagram: @JaredFreid) is a New York City based comedian who you may have seen on MTV, The Today Show or hosting the ever popular Betches of Comedy tour. His dating advice has been featured by books published by Simon And Schuster, on TV, and on the internet. We’ve asked him to give us some insight into the minds of that assholes we usually date. Send any of your dating questions to firstname.lastname@example.org
Q. A good guy friend and I have recently been flirting – known him for 7 years good college buddy. Flirting is mutual and lately I've thought to myself ok I think I have a crush on him. Good or bad idea to test the waters ? I don't want to ruin a friendship but would love to see where something goes romantically.
It’s always a good idea to test the waters with a friend because, if this is even a thought, then you’re not really friends. Look around you ladies, there’s a bunch of guys you know. They all have a reason for being in your social circle. The more circumstantial the reason the more these guys know a creepy amount about your Instagram posts from 77 weeks ago. This means, the guy you grew up with, he’s a friend. The guy who had the same econ class, he thinks about your nipples. The guy who was best friends with your ex, he's probably your friend. The guy you g-chat every day that went to college with your friend from camp, he discusses your ass (at length). Becoming a “good college buddy” was his way of getting close without getting turned down.
And honestly, the same could probably be said about you. Any time either one of you sent a text, or did the other a favor, or discussed the other’s hookups it was done with you in mind. You inserted your feelings into that talk to make it so that YOU could get closer. We all do it. It’s totally normal.
I understand your fear. This is someone that makes you feel good. Considering this post-college gap that most of our parents never dealt with, these are some lonely years. Parents are asking crazy questions like, “Why would a 25 year old still be on a family plan?,” friends are getting their own relationships, and siblings are either older with babies or younger living a life we wish we still had. So anyone that person that still texts us and is living the same nightmare is someone you’d hate to lose. But, the minute you find a relationship this “college buddy” is going to fade into the mist like a guy who said he “had a really good time” after a first date. He, most likely, won’t be at your wedding, or know your kids, or be friends with your husband. He will be some guy you had a thing for once that you’ll wonder what could have been when you see him out for ice cream with his own kids.
So lets make a move with these “buddies” we are “kind of into” and get on the road towards a probable ending of, “Hey, I’m just really busy right now.” Send him a text saying, “We should get drinks.” He will come back with some version of yes or maybe. A “Maybe” means, he’s not into it. Don’t ask why or take it personally, just back off and hang out with your real friends. A “Yes,” is done in the form of actions. Be a little forward just to be clear that this isn’t to go over college scrapbooks. Give him a day of the week that you’re free and an area of town you like and then let him pick a place. He will make this happen if he’s interested. At this point you will have pushed hard enough to give him half an emoji eggplant. Then, when you go out, go with it. Have fun. Get a little drunk. Don’t go past second base.
That’s my final piece of advice. The “friend” that becomes a hookup happens really really fast. Sex comes really easy because you’ve already built up trust before this ever got romantic. As friends, you knew each other’s majors, hometowns, family situations, and favorite TV shows so the only mystery is what position makes you orgasm the easiest. Relationships are a lot like sex, the faster he climaxes, the less fun you’ll both have. So try your best to keep that in your back pocket for a realistic amount of time. Hold onto that mystery and that can give you a real chance to see if this guy should have just stayed a “friend.”