Ask Her Out
Ideally, this should be done in the first message for best results. Again, I know this may seem like an aggressive approach. Shouldn’t you ease your way in? Test the waters with humor? No. No one has time for that, and carrying on a conversation for too long before initiating an IRL meeting is actually more of a red flag in today’s online dating landscape than the opposite. Yes, back in 2013 the idea of texting back and forth with a Tinder match all day everyday was all the validation anyone needed or wanted from a dating app, but times have changed. If you spend too much time messaging, we assume you’re either a catfish or a flake. So, I repeat, just ask her out.
This can even be an effective way to resurrect a conversation that has fizzled. Sex party guy and I had exchanged a few messages back and forth a few weeks before he extended the invite that finally got me to leave the apartment.
Be specific
A vague “I’d love to take you out for a drink sometime” is a start, but you’ll probably get further with “I’ve been meaning to check out this cool bar that just opened. Any interest in joining me Thursday night?”
1. It shows that you are a competent person who is capable of making plans. Wanna know a secret? This automatically puts you above the vast majority of men! Yes, the bar is really that low!
2. A specific event/location gives her some added incentive to say yes. I’ve gone out with guys I may not have otherwise agreed to go out with simply because they suggested a cool-sounding restaurant or a bar I’d always wanted to go to (or, you know, a sex party). Should the mere idea of going out with you be enough without any extra frills? Sure, maybe. But she doesn’t know you. If you want her to go out with you instead of any one of her hundreds of other matches, you’re going to need to sweeten the deal a little.
Follow up
Suggesting specific plans also works to your benefit because it makes it seem more likely that those plans will actually happen. As you may have gathered, the dating app landscape is an extremely flakey place. Every day millions of app-daters make vague plans that never come to fruition. I just made that up, but it’s probably true. If you instead propose clear, concise plans, your prospective date will think, “Hey, it sounds like that date could actually happen,” which will make her more likely to agree to it.
However, please remember that even the best-laid plans do not actually exist if you don’t follow up day of. Made firm, solid plans to hit up Thursday’s sex party on Tuesday? Great. But you still have to follow up to confirm on Thursday, otherwise your date will assume you’ve flaked. In 2020, we all presume ourselves ghosted until proven otherwise.
The state of online dating today is a cynical affair, to be sure. But ultimately, it’s still just dating. Don’t overthink it. As Too Old to Date podcaster Brad Garoon told InsideHook last year, “If you 
pick the time and place to meet, make it a convenient location for your date, and confirm that it’s happening, you’re already doing better than a great portion of your competition.” Especially if that convenient location happens to be a BDSM dungeon.
Take it from me, a seasoned app-dater who is at once young and haggard: If you have any intention of taking a connection off your phone and into the real world, it needs to be initiated ASAP. Here’s how to do that in three simple steps.
