How to sched­ule mul­ti­ple dates in one night

With so many sin­gles on so many apps, it can be dif­fi­cult to fig­ure out how to fit them all in

The Hamilton Spectator - - LIVING - LISA BONOS

When Lisette Py­lant re­al­ized that her date Mon­day night had planned sev­eral other dates at the same bar — each woman com­ing in one af­ter another — she was out­raged.

She live-tweeted the en­tire night, jok­ing about there be­ing a rose cer­e­mony later. Ac­cord­ing to her tweet thread, she peeled off with this guy’s dates and de­camped to another bar across the street.

This man was not smart about his multitasking. But there is noth­ing wrong with schedul­ing more than one date in a sin­gle night. With so many sin­gles on so many apps and more first dates hap­pen­ing than ever be­fore, it is hard to fig­ure out whom to meet and how to fit them all in.

Sure, it’s ro­man­tic when you have those first dates that start as a drink in a one spot and then be­come din­ner some­where else and then turn into a ram­bling “Be­fore Sun­rise”-es­que walk all around the city. But Richard Lin­klater is not di­rect­ing your love life, and Ethan Hawke is taken. Chances are, you won’t want to spend the en­tire night with a stranger you just met from the in­ter­net.

So if you have the time and en­ergy for more than one first meet­ing, go for it. Just do it re­spect­fully. Here’s a guide.

• “Pre-dates” ab­so­lutely are a thing. Py­lant com­plains that her date con­sid­ered his mee­tups not dates but “pre-date” con­ver­sa­tions.

The “pre-date” is a term I’ve used be­fore. Namely to de­scribe a meetup be­tween two peo­ple who’ve first con­nected on the in­ter­net and then de­cide to have a real-time in­ter­ac­tion with one another. It’s a “pre-date” be­cause you’re nearly strangers to each other; you have no sense of whether there’s chem­istry with some­one from look­ing at their on­line pro­file. A “pre-date” can hap­pen at a bar or cof­fee shop, or over the phone. (One of The Wash­ing­ton Post’s con­tribut­ing writ­ers reg­u­larly FaceTimes with po­ten­tial love in­ter­ests be­fore meet­ing up, and he cred­its the tac­tic as time well-spent.)

Ac­cord­ing to her Twitter thread, Py­lant and her date had al­ready met once — at a bar — be­fore agree­ing to meet up again last night. So in her case, this wasn’t a pre-date. But he did sched­ule other pre-dates with women from dat­ing apps, who started show­ing up af­ter Py­lant got there. Which brings me to my next point.

• If you’re do­ing a dou­ble­header, sched­ule your dates in dif­fer­ent lo­ca­tions. What­ever you’re call­ing it — first date, pre-date — do not sched­ule back-to-back dates in the same lo­ca­tion. That’s a recipe for dis­as­ter, whether there are six women lined up or two.

If this guy wanted to do a pre-date con­ver­sa­tion with some­one over the phone, then meet Py­lant in per­son and then meet another woman in the same evening, that’s all fine. He just should have done them in dif­fer­ent spots.

Imag­ine this: If you had din­ner plans with your best friend at 7 p.m., and you let him know that you had drink plans with another friend at 9:30, would your din­ner buddy leave in a huff or live-tweet about how rude you were be­cause you didn’t re­serve the en­tire night for him? I hope not. That sounds like one self­ish friend.

So why do we ex­pect a first date to last the en­tire night? That’s un­re­al­is­tic, and it’s an ex­pec­ta­tion that prob­a­bly stems from a life­long diet of ro­man­tic come­dies. Nowa­days, the ex­pec­ta­tion is that first dates should be kept short and sweet, re­gard­less of whether you have another one booked that same night.

• Set ex­pec­ta­tions from the get-go. If you have to be some­where else at a cer­tain time, let your date know up­front. On a first date, it’s per­fectly ac­cept­able to say: I need to be out of here to meet at friend at 8 p.m. or to watch “The Bachelorette” fi­nale or feed my cat. Maybe your 8 p.m. es­cape plan is ac­tu­ally a sec­ond first date. Or maybe you know that all you can han­dle is an hour-and-a-half of first-date chit-chat. There’s noth­ing wrong with set­ting a time limit on a first date. You’re nearly strangers; you’re show­ing up for a test drive, not for a long-dis­tance road trip.

• That said, no more than two dates in a night, tops. It seems that Py­lant’s date was cu­rat­ing his own speed-dat­ing night. That’s fine at an ac­tual speed-dat­ing event, where the pre­sump­tion go­ing in is that ev­ery­one has mini-dates with lots of peo­ple. But if you’re mak­ing plans with some­one in the real world, they’re ex­pect­ing your un­di­vided at­ten­tion for the amount of time you’re to­gether.

Pre-dates ab­so­lutely are a thing. They can hap­pen at a bar or cof­fee shop, or over the phone.


If you’re do­ing a dou­ble­header, sched­ule your dates in dif­fer­ent lo­ca­tions. Oth­er­wise, it could be­come awk­ward.

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