The amount of time you and your dates have been seeing each other matters.
Gottsman says that this is a good set of rules to adopt if you're looking to ethically double up. "Once you've decided whether or not you like a person, you should stop double-booking on them," she says. For me, that's two dates. It might be different for you. But Gottsman is clear about how you should only double-book during the early stages of dating — when you're first getting to know a person.
Drinks followed by dinner is fine. But coffee followed by drinks is better.
Gottsman says this variance not only helps make sure you're in a good headspace for both dates, but also gives you a little breathing room, too. "If you decide on a lunch for one person and a dinner for another, that could be considered double-booking, but that's also something you'd do with friends," she says. It also ensures that you're not asking date number two to meet you in the same place as date number one — a big no-no in double-booking.
Try to keep at least an hour buffer between dates.
"It's important to space out the dates, too," says Gottsman. "It just ensures that you're being respectful of everyone's time." It also decreases the chances you're going to flake on date number two because of traffic or a delayed subway — which, thanks to the universe, would always happen to me when I was running late for date number two.
Never flake less than three hours ahead of a date.
But this goes both ways. In order to make sure your first date isn't offended by your sudden need to bail, it's always a good idea to give them a heads up before you meet up that you'll have to dip after a couple of hours. "That's actually preferable for a first or second date," Gottsman says. "It's sometimes better to have them be shorter. You're really just getting to know [the person]." Plus, I always like to leave a date in the same way George Costanza learned to leave any situation — on a high note.
Prepare for awkwardness if you get caught.
I've only been caught once. (I thanked the guy who I'd gotten martinis with for the nachos last night.) And when I was called out, I just tried to play it cool and make a joke. "I had a really busy week and I wanted to meet you, but I'd already committed to another date, too. Can I buy you a drink and make it up to you? I promise you that you'll be the only guy I'll see that night."
"You were honest," Gottsman says. "That makes it a lot easier for someone to forgive you." And forgive me he did. We met for another round of martinis — and he was, in fact, the only guy I saw that night.