How to Double-Book Your Dates and Still Get an Etiquette Expert’s Blessing

Photo: Getty Images/Geber86
Anyone who has ever dated online knows the cold, hard truth about what a time-consuming black hole the undertaking can be. With so many options on your apps, scheduling dates can become more difficult (and less enjoyable) than scheduling an in-network dentist appointment. So it should come as no surprise that from time to time, some people decide to double-book, dating two people in one night. This means meeting potential suitor number one for an early cocktail or matcha followed by a dinner with potential suitor number two.

As someone who's done it and lived to tell the tale, I can say with certainty that people have got feelings about this course of romantic pursuit. When I talk about my double-booking experiences, a good number respond with shock, some say its sounds exhausting, others say it's unfair to the dates in questions, and a confident few admit to having done it themselves. Since the verdict is clearly out on what's acceptable here, I chatted with national etiquette expert Diane Gottsman about whether or not I was breaking any kind of decency rules by setting two dates in a day.

Here answer, not shockingly, was complicated. “When you double-book, it’s because you're hedging your bets,” she says. “You may not be giving each person your full attention because you’re busy worrying about the other date of the day.” If the date in question is only a first or second date, then that’s not necessarily a big deal. “It’s when you’re double-booking with people you’ve been dating for a while that this gets tricky,” Gottsman says.

“It’s when you’re double-booking with people you’ve been dating for a while that this gets tricky." —Diane Gottsman, etiquette expert

The timing of the double-book is also important, she says. “We do this with our friends all the time,” she says. “You might meet one friend for lunch, and then another for after-work drinks. That’s not necessarily double-booking.” So if you’re going to see more than one date in a day, don’t stack the times on top of one another. Instead, spread them out. Have a day date with one, followed by an evening date with the other.

And if you do need to schedule the meet-ups close together, then at least be open about it. “You don’t necessarily have to tell them that you have another date after this one,” Gottsman says. (That would be…bold.) Instead, just disclose that you have a dinner to scoot to after. That way, you’re not being deceitful, and you don’t have to worry about lying to your date in order to hightail it out of there faster.

The bottom-line when it comes to double-booking, Gottsman says, is to just remember to act with integrity. “Own up to what you’re doing and why you’re doing it,” she says. “It’s all about respect in relationships. So as long as you’re being respectful of your date and their time, you don’t have to worry about being deceitful.”

Speaking of respect, dressing appropriately for your date is a great way to convey it. Plus, if after all the double-booking, you find yourself coupled up with one partner, should you worry about spending too much time together

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