The PGP Weekly Dating Q&A: Valentine’s Day For New Couples


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.

Q. This guy and I have been dating for a few months. He hasn’t even mentioned Valentine’s Day and I’m wondering if he will even say “Happy Valentine’s Day” never mind take me out. I also don’t want to seem like the “crazy chick” who is too into Valentine’s Day. If we don’t go out, is this a sign?

I’ve received more than 30 messages on HeTexted that look exactly like this one. Every girl starts by describing the length of her relationship like your 6-year-old nephew explaining that he’s “actually six and four months,” and then she asks what she should expect. The question makes a lot of sense. The 2014 version of Valentine’s Day is confusing. Ask any couple how long they’ve dated and they look at each other like someone dropped a baby at their doorstep. It’s almost like they’re trying to telecommunicate to one another the questions they want to ask, “Are we starting from when we met on Tinder?” “Have we even said that we’re dating to someone out loud?” “Does him stopping me mid-blowjob and saying ‘I really like our time together’ mean we’re engaged?” Since our relationships have this vague starting point, it’s hard to know what to expect on a day we’re told to expect something. Below, I’ve broken down the various stages of relationships into best case (and worst case) scenarios. I’ve followed it up with an honest breakdown that would make a whole group of girls at brunch exclaim in unison, “I just can’t!” Good luck tomorrow.

One Date, Multiple Weekend Hookups

Best Case: A text that says, “HVD” with any emoji
Worst Case: He tweets, “Valentine’s Day? More like, “Vagina All Day Day!”
What Your Friends Won’t Say: I know it’s Valentine’s Day and everyone wants a little bit of attention, but complaining to your friends that “Jason only sent a text” will make their eyes roll harder than a girl wearing neon at an EDM festival. Take some ownership of your hookup that’s going nowhere and do one of two things: something sexual with this person you’d never do with your future husband or end it. This person is a waste of time. All you are is a canvas for a paint brush technique he calls sex.

Three Dates, You Haven’t Had Sex Yet

Best Case: Dinner and drinks, nothing over the top, acknowledgement
Worst Case: Nothing or he goes all out
What Your Friends Won’t Say: I’ve always wanted to make the most honest dating website profile ever by simply writing, “I won’t know if I like you until after I climax.” And really that’s where you and him stand. If he’s pushing so hard to romance you on Valentine’s Day, it’s because he just wants to get that seed out of his system so he can start thinking clearly. If he does nothing at all, then he thinks a date with you is getting further into the “he’s still dating me without sex so this is serious” rabbit hole. You want him to run into this date like Emmit Smith scoring a touchdown, like he’s been here before.

Three Dates, You’ve Already Had Sex

Best Case: Dinner Date
Worst Case: Nothing
What Your Friends Won’t Say: He needs to acknowledge that the day exists. That much is a win. A text, email, or call would really be great because he’s saying, “You’re the one I’m thinking of on the day I have to think about this stuff.” I know you want more than a text, but his biggest concern is making sure you know that sex to him is just a blowjob with your vagina.

Dating Over A Month, He Is Not Introducing You As His Girlfriend

Best Case: Flowers and a dinner that made him dress up a bit.
Worst Case: A rose emoji
What Your Friends Won’t Say: I hope you’re still using condoms. If you hit that “best case” then things are good. He’s down to date and is making his best effort even though he may be slower than you want. If you’re closer to that “worst case,” then you shouldn’t start planning dates for next Valentine’s Day. You actually shouldn’t be making plans with him for the rest of the weekend. Even if you did, I’m sure his battery will run out or he’s spending this weekend on a subway platform.

Dating More Than Six Months, He Introduces You As His Girlfriend

Best Case: He plans a dinner, dresses up, and brings flowers
Worst Case: He texted you this week, “I’m up for whatever. What do you want to do?”
What Your Friends Won’t Say: If you want more than that “best case,” then nothing will really ever be good enough. You should just spend your days watching romantic comedies and then marry a body pillow you’ve named Mr. Gosling. The “worst case” is the toughest pill to swallow. Making a plan for Valentine’s Day makes him look more attractive to any girl. If he doesn’t get excited for that after three months, then what will ever motivate him? Will he care enough to celebrate your one year anniversary? Will he know when that even is? Will he text you after you have your first born saying, “Good job, dude?” I see this all the time. Couples become old couples too quickly and then girls stick around because it’s easier to have a boyfriend than it is to find a better one.

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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