Here's How To Successfully Double-Book Your Dates

Photographed by Rockie Nolan.
One of the biggest conundrums I run into as someone who prioritizes her dating life is time. I'm busy. Free nights are precious. And every once in a while, I run into a situation in which two people want to meet up with me in one weekend — a weekend that already has other engagements penciled in, too. So what do I do?
I double-book.
Now, I know there are a lot of contentious feelings around double-booking — especially after that viral story of the guy who booked six dates in one night. (So many rookie mistakes there, pal.) But according to Diane Gottsman, national etiquette expert, author of Modern Etiquette for a Better Life, and founder of The Protocol School of Texas, double-booking is totally fine when it's done correctly. "In the early stages of dating, especially when it comes to online dating, you're just getting to know people, so you don't necessarily owe them a lot," she says.
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I obviously agree with her wholeheartedly. I'd even go so far as to say that lining up a couple of meet-ups in a day is an extremely economical way to get a good sense of what you're looking for in a partner. So, ahead, I lay out my tried-and-true rule book for doubling up on your dates, culled from years of experience, with an assist from Gottsman. Following these steps has helped me avoid all of the messiness of dating in multiples — viral infamy included.
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The amount of time you and your dates have been seeing each other matters.

My golden rule of double-booking is this: Once a partner and I get past date two, I no longer book other dates on days that I'm already scheduled to see them. And, if I've already got a date on a day they suggest, I'll offer another date for us to meet up (rather than just saying "that doesn't work for me").

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.
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Drinks followed by dinner is fine. But coffee followed by drinks is better.

The first time I attempted to double-book, I stupidly agreed to back-to-back meet ups at two separate bars. As someone who gets dizzy after a glass and a half of wine, this was a pretty major screw up — especially since I hadn't eaten before either date. So after that, I learned my lesson, and always made sure that if date number one was drinks, date number two had to either be coffee before or dinner after.

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.
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Try to keep at least an hour buffer between dates.

So much of the success of this feat is timing — especially if you're booking two meet-ups close together. When I was setting up two dates in one night, it was like solving a math equation in my head. I'd want to allocate at least two hours for the first date, in order to give us enough time to drink our drinks or have our coffee. Then, I'd buffer in at least two hours between dates, to account for travel time and whether or not the date ran over.

"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.
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Never flake less than three hours ahead of a date.

Speaking of flaking, remember that it's never a good look to cancel a date right before you're meant to meet. When double-booking, you're going to run into situations where you really like date number one and are tempted to bail on date number two in order to extend your time with the first person. But, in my opinion, it's rude to do this — even for any of the excuses I know are bubbling up in your brain right now. "Issues arise when you're being deceptive, and when you're canceling dates," says Gottsman. "It's a waste of the second person's time."

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.
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Prepare for awkwardness if you get caught.

Look, regardless of how well you might play the game of double-booking, sometimes you might get caught. You could mix up names or go to the wrong bar. And that's fine — it happens to the best of us. In my experience, the best thing to do if this happens is to just fess up. Don't get defensive, and don't try to lie — you'll just dig yourself deeper into a hole.

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.
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