Advice and Insights for Modern Daters

From App to Date in 24 Hours or Less

Corporate Bro shows how to use sales methodology to lock down a date.

Q. I’ll get straight to the point: I can’t figure out how to convert a dating app conversation to an actual date. Every girl I message with either stops responding mid-conversation or never responds in the first place. This makes no sense to me, since we obviously matched for a reason. What am I doing wrong here?  

Sean, 26, Hartford, CT

A. All right, Sean. People frequently ask me how I have found so much success on dating apps; “success” being getting off the dating app and into real life. That’s the goal, and we’re going to make you successful. 

I’ll preface my explanation by saying this: I’m not successful because I have the face of John Stamos, circa Full House Season Three. In fact, I consider myself a soft 6-7 on a scale of 10, depending on how hard I try. Unfortunately, many men use their physical appearance to explain their lack of success on dating apps. I don’t buy it. Anyone can be successful on dating apps; for me, my experience as a software sales guy has shaped my approach and all but eliminated the following common problems:

  • Stalling of the conversation
  • Ghosting during the conversation
  • Flaking before the date
  • Cancelling the date

Here’s the thing to remember: until you meet in person, app dating really is about selling yourself. This is not game playing — it’s just reality. Why would he or she take time from their busy week to spend time with you, a stranger? Why not someone else? What can you offer during the conversation phase that someone else isn’t? What will motivate your match to move the conversation offline and into real life?

Like in sales, the process of going from match to date has a cycle of its own. The cycle usually goes something like this:

  1. You match, and soon after drop your go-to pick-up line
  2. The two of you begin a slightly sarcastic, flirty conversation
  3. The conversation ultimately fizzles out, leaving you with another ‘what-could-have-been’ tale of dating app woe

How does one avoid the dreaded third stage?

In sales, there’s a name for this: we call it the “Upfront Contract” or UFC. In short, the UFC is where you state your agenda and the potential outcomes. You set the expectations. The best part of dating apps is that when you match or someone responds, there is already a connection. In sales, that’s called a hot lead. You already know your match is interested and listening. This means you can skip the mind games and “What’s my reason to talk to him/her?” and go straight for what you want — a date.  

76% of Hinge matches that turned into dates involved a phone number exchange within the first 24 hours.*

An example of an upfront contract might look like this:

Me: When I message someone on this app typically one of two things happens: we either start a weeklong text thread that one of us eventually loses interest in, or in the next couple days we get drinks and see what happens. Obviously my goal is the latter. Where is this one going?

This may feel uncomfortable at first, but by calling out your goals and outcomes, you effectively put the ball in their court. The truth is, many women prefer a guy who is forward. If you don’t believe that, let this fact speak for itself: 76 percent of Hinge matches that turned into dates involved a phone number exchange within the first 24 hours. You have got to be proactive. 

By the way, your upfront contract doesn’t have to be as formal as the one above. Make it yours — mention a specific restaurant or bar, a hobby you’ve noticed in one of her photos, anything. Tone the humor up or down in accordance with your personality. As long as you call out your goal (meeting in person) and potential outcomes (the conversation goes nowhere, or you meet and go on a date) you won’t waste time.

Sometimes though, it’s unavoidable  — you’re stuck in the never-ending cycle of small-talk, and you’re desperate to know: are you two ever going to meet, or is this person at best a pen pal, at worst, a catfish?

Here’s what to do in that situation:

Me: Look, I’ve enjoyed our conversation, but my fear is we are going to keep doing this until it gets boring and I’ll never get the chance to you meet you in person. There is this new spot called X, want to go on Wednesday and continue this in person?

You just called out the elephant in the room (the time wasting text thread) and stated your goal (a date). You are prompting an action. If they continue to dodge your upfront contracts then you should probably cut bait.

In the end, match-to-date is about qualifying or disqualifying potential mates as efficiently you can. All dating — whether you meet in person or online — is a numbers game. Don’t spend all your time on one match — especially if you haven’t met in person. There is no guarantee you’ll connect, so it’s best to use your upfront contract. Be direct, be classy, and Always Be Closing. 

*Hinge user data

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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 Corporate Bro questions at


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