Chapter 2: Getting Off The Bench

How to go from Match to Message

Trust us, this whole new dating app concept is new and weird and pretty awk…and most of us haven’t ever used a dating app – so how the heck does this all work? How do you get from Match to Malbecs? From heavy vetting to heavy petting?

Rumor has it that, even amidst our fool-proof screening process, there are still some flakes on The League. And by flakes we mean: guys and gals who match but don’t message. Lame… but, let’s be honest, we’ve all been that dude/dudette, so let’s not judge anyone too harshly here.



We thought we’d combine some basic pointers, while also incorporating feedback from our users and examples of good and, well, not-so-good texting game. The hope is with The League you will meet great people that you wouldn’t normally have met in real life. Maybe your special someone doesn’t hang out at [insert yuppie bar name] every Friday like you do. Or maybe they’re at expensive destination weddings every weekend just like you were last year. That’s where The League comes in to make sure you don’t keep missing each other.

Let’s be clear: the goal is to meet in person as soon as possible. Hey, if it turns out there aren’t any sparks, well, at least you met someone cool. You won’t know until you go.

You got through the first hurdle: not getting rejected! Congrats hot stuff! What to do next?

Scenario 1: You got the Home Run. Onus is on you to initiate the conversation since you’re the one who clearly has the app open, silly. Girls, don’t be shy, this is 2015 and we know you’re handy with that keyboard. It’s not like you’re asking the guy on a date, you’re just saying hi!

Note: Boys, even though we believe girls should message first just as much as guys should, we’re all smart enough to understand data/statistics and know that this gender behavior change won’t happen overnight. In the meantime, realize there’s many a girl out there that expect you to send them the first “hello!” Don’t be a slacker.

Scenario 2: Your match got the Home Run. You just got notified, but the other user hasn’t messaged. Chill. There’s a ton of people out there who have anxiety about what they should send as their first message or are totally new to this mobile dating app world. Relieve their stress and just send something to break the ice – even a “Hey [Name] how is your Monday going?” is better than nothing! Remember, you both expressed interest already, so you’re already through the awkward part!


Scenario 1: Your match has no game. Go easy on them. Not everyone is as funny and witty as you are, you rockstar. We’re guessing what they lack online, they make up for offline. And, hopefully they will read Chapter 2 and will pick up a few tips to improve. Take a chance and meet them anyway, even if it seems they don’t understand sarcasm. We promise there’s likely something redeeming about them or they wouldn’t be on the League… and if it turns out we’re wrong, well, report back to your concierge and we’ll put them on watch….

Scenario 2: You stuck your neck out there, and your match doesn’t write back. F’ em. No, just kidding. Don’t get your feelings hurt. There are a couple potential reasons here:

  • They’re busy. They haven’t seen your message yet. They could have their push notifications turned off and have forgotten to login. Just give it time and don’t start doubting yourself. Leaguers are busy (duh, that’s why they chose this app) and they’re not desperately checking dating apps every hour. In fact, some of our favorite users login only 3x/week but make a point to meet all their matches in person. We think that’s cool.
  • They’re almost off the market. They could be dating someone now and are slowly winding down their League useage while they determine whether they should DTR with this new person. Comparison shopping, one could say. Hey, it happens, so don’t get too upset about it. Better to be on the bench that not even on the team, right?
  • They’re turned off by your messaging game. They thought your opener was lame. Or offensive. Or just weird. The good news is that this one is the lowest hanging fruit of all the ones above and the most fixable.
  • They lost interest in you. How could this be after you guys both accepted each other!? you may ask. Well, for one, if you’re disguising what you look like, they very well may have found you on one of those other-social-networks-that-will-remain-nameless and decided you were selling a false bill of goods. Eek. But, it happens. You know you’re a badass, we know you’re a bad-ass, so own what you look like and don’t hide behind sunglasses, crazy Instagram filters, or force anyone to play Where’s Waldo with a bunch of look-a-like clones.


Nexy time, we’ll actually critique your messaging game. Send any examples of good game/bad convos to