Advice and Insights for Modern Daters

Stuck in the (Date Five) Mud

Corporate Bro counsels a letter writer whose relationships fail to progress past the fifth date.  

Q. What are the signs that a guy is NOT serious about moving forward towards an actual relationship with you? I’m 27 and feel like I constantly get caught up in this endless cycle of going on dates with a guy, sleep together around date 5, and then it never gets more “official” after that — it just stagnates. For example, they won’t want to see me more than 1-2x per week, they’ll keep their weekend plans with their friends as a priority over hanging out with me, etc. But, it’s not like anything is WRONG. Things just don’t progress. What am I doing wrong? Or am I picking the wrong people? How can I avoid getting into this situation again?

Hannah, 27, Philadelphia, PA 

A. Let me start with a compliment: You must be very hot if guys are sticking around until date five – especially if their motive is simply “that ass.” Now admittedly, when I read the first sentence of your question I assumed you were banging on date one. That of course, would be too simple a fix. You are going to have to be a little more observant during the first five dates in order to weed out the hit-it-and-quit-it types. Trust me, I’m one of them.

One of the first places I would look for signs is the date plans themselves. Were you the only one making the plans? Were the activities all your idea, all his, or a mix? Was every one of his ideas either centered around drinking or Netflix and chill? Was any real effort or thoughtfulness put into the location or was it just “that dope spot?” If looking back you notice that heavy drinking (or Netflix) was involved in every situation, that’s a red flag. He was just trying to get your guard down. THE DUDE WANTED TO BONE.

Secondly, what were your conversations like? Sure some sarcastic banter making fun of the fact you watch Teen Mom will surface, but did it get any deeper than that? How often are you comparing lists of the things you both like? Lists never allow you to peel back the layers. It stays very surface level.

Did you get to hear a lot of stories about “me and my bros?” If so, there is a good chance this guy hasn’t considered a legitimate relationship in awhile. Guys who are looking for something serious will not only keep the topic on you, but try to get beyond the base level facts. For example, it’s easy to ask what you do for work. “I work for ‘X’ company.” The serious guy will take it one step further: Why did you take that job? What aspects of that job do you like and why? What’s the goal beyond that? No matter their goal, if a guy knows what he’s doing he’s going to let you do the talking (and talking… and talking…), so you have to pay attention to the substance of the conversation (or lack thereof) to know the difference between trying to get in your pants and trying to get into your heart.

Now let’s discuss weekend plans. The dopest girls, the keepers, the winners, are the girls who can hang with the bro group. If you never get invited to come hang with the bro group, he is trying to keep you at a distance. DO NOT expect to be invited to every bro event, or even most bro events for that matter. Let’s face it, we bros need our bro time. But, if you ever get that elusive invite, THAT IS A BIG DEAL. I could probably write a whole different article about how to act when you get to hang with the bros so I won’t even go there. Bottom line, don’t fuck that up.

Okay, so we have talked about the bro in this situation. Let’s talk about you now. Are you boring? Are you sure? Let me ask this again: ARE. YOU. BORING? Okay. Assuming you are not boring (please don’t confuse basic with boring), then perhaps you are knowingly rejecting the signs that the guy isn’t what you think. Maybe he seems really cool. Maybe he’s super hot. Are you letting yourself ignore the red flags? I truly believe a lot of women allow themselves to get played. You have so much power during the beginning of relationship YOU DON’T EVEN KNOW! Own it. Make him prove value, not the other way around.

I’ll end with this. I know a lot of people who go on five dates. I do not think that is some absurdly high number or that you should feel bad about it. You asked for tips on how decrease the amount dates necessary to find out how serious a guy is. Truth is, if you really want to know – ASK! Probably not date one or two, but definitely by date three it is a fair question. Put him on the spot. See how he responds. The dating world will always be a numbers game and call me a pessimist, but there is no such thing as “The One,” so you simply have to keep searching until you find something that works. If you see red flags, don’t waste your time. Instead, tell him you are looking for something else and MOVE ON. So long as you keep going and keep your eyes open, eventually you’ll find yours.

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Corporate Bro (aka Ross Pomerantz) is a 20-something software salesman turned-social media influencer living in San Francisco. His viral Instagram account, @corporate.bro, hilariously depicts the mundane yet relatable foibles of millennial office life. Send questions to Corporate Bro at


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