The PGP Weekly Dating Q&A: Texting A Guy With A Girlfriend


Jared Freid (@jtrain56) is a comedian and one of the “Bros” at HeTexted is a site where girls can get advice on the texts they receive from guys. Every Thursday on PostGradProblems Jared will answer one of the questions from his HeTexted mailbag. These are real questions from real girls visiting the site each day. If you have any of your own dating questions go to and ask Jared or any of the other Bros that fit your particular situation.


Him: I think you’re pretty
Me: Aww thanks 🙂
Him: But I have a girlfriend…
Me: Yeah I know haha
Him: Yeah
Me: What does that got to do with it?
Him: Nothing haha, I was just saying it

This was the conversation we had after a party where our friends hit it off. He says nice things like this all the time. Is he being nice or trying to see if he has a shot with me?

Girls live in this world where they think guys have the privilege of never feeling lonely. They think that when we end a relationship, we walk into a party out of a Bud Light commercial where the hot waitresses have flirty comebacks based on our beer order. The fact is, it’s very much the opposite of that. A relationship ends and we are like a house kitten being let out into the wild. We have no idea how to feed ourselves because we just spent months where our “move” was pointing at our boner. Try that in a bar and see what the police say when you exclaim, “It’s all I know!” After a relationship guys are rusty at talking to girls and those waitresses don’t even acknowledge that we ordered a Budweiser. A Budweiser! Like a man!

This isn’t a call for sympathy. This guy is a jerk who’s afraid of feeling uncomfortable at the bar on his own. I explain that fear to answer why any guy with a girlfriend, that you obviously know about, would ever send a text. It’s easy to say that he’s “just being nice” and that you guys “are just friends” but a guy with a girlfriend only has so much time. He has his friends, his job, and his family. And that doesn’t even include his girlfriend who emails, texts, calls, Snapchats, pings, prods, and gets annoyed when he doesn’t get back to her within five minutes. So where do you fit in? He’s not putting aside an hour of his day to tell you that you’re pretty without any chance of smelling your hair.

Most girls know the answer to this question before they even ask it. Look at the girl in this example. She didn’t really get upset because she likes to be called pretty (who doesn’t?). Now he knows he can keep flirting and she won’t report him to his girlfriend. If his girlfriend sees the texts then he has deniability of tone, “Oh that’s nothing, she was really upset that night.” And when he finally mans up and ends this thing, he’ll have thrown himself what I call, the “Hookup Alley-Oop.” An “Alley-Oop” happens in basketball when a player lobs a pass to his teammate to dunk the ball. Relationship version of this guy is lobbing a hookup to the single version of himself. Now, he walks into that bar freshly single without the struggle of being alone. He has a freshly flirted girl ready to start things up.

My advice to any girl in a similar situation is to move on. The guy you’re texting will either find his balls and end things to pursue you or, more likely, he’ll find a new girl to flirt with over text. Right now, you’re wasting time that could be spent texting new guys who don’t keep their phone turned on it’s face everywhere they go. The fact is, if you’re an alley-oop now then you’ll probably get alley-ooped by this guy in the future.

Jared Freid is a comedian and HeTexted “Bro” based in NYC. You can ask him dating questions at or find him on Twitter (@JTrain56) for weekly columns, podcasts, and videos.

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Jared Freid is a NYC based comedian. He has been featured on Tru TV's "NFL Full Contact" and more recently on MTV's "Failosophy." He is also a writer for The Huffington Post, The Fan Hub, Weekly World News, TotalFratMove, BroBible, and HeTexted. If you're not the reading type, Jared created the "Frat Dude Goes To" series where he travels the country interviewing "Bros" at wild events like the Carolina Cup and the AVN Awards. Follow him on twitter @JTrain56 for all of his weekly content.

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