A Matchmaker’s Essential Tips for Nailing a First Date

Nowhere on this list does it say, “pretend to be interested in that super-boring thing they love to do.”

By: Laurel Pantin
Illustration: Meghann Stephenson

Dating in 2017 is a strange landscape—it all happens super fast and with Bumble, Tinder, Her, Huggle, and probably about a dozen apps we’ve never even heard of yet, you can shuffle through potential partners as easily as you can order lunch. But what if you happen to *really* like the person you’re about to go out with, and you’d *really* prefer that this date ends in a nightcap instead of more endless swiping?

Emily Holmes Hahn is the founder of LastFirst, the bespoke matchmaking club our co-founder, Stephanie Mark, just tested out. For the times when you’re about to go out with someone you think you might seriously click with, Hahn gave us her three top tips for nailing that first date.

 

Should you or should you not Google your date before meeting?

“I really discourage online ‘research’ in advance of a date. A little discreet social media stalking is fine, but tracking your date’s every career and social move online is weird and will make you less comfortable when you’re finally together in person. Nobody wants to be the girl who slips and says she already knows what her date has been up to that week, who they’ve been chatting with, or even general things like what their hobbies and interests are. These things should be discovered organically—they are part of the fun of getting to know someone new! If you do make a faux pas and mention something you’ve seen on social media, just GO WITH IT. It’s better to say, ‘I saw you were at the Standard this weekend, that looked super fun!’ than ‘Oh I saw you were at the Standard this weekend,’ and then backtrack, ‘Uhh, I forget where I saw that! I must have been bored and looking around on Instagram.…’”

 

What are some easy conversation starters in case you run out of things to talk about?

“It’s best to go with the flow, so you should really try to segue naturally from what you’ve been talking about with a relevant anecdote or a thoughtful question. If that isn’t working, I think pop culture can be a fun reference for a first date, while also opening the door for some smart banter. Watching the TODAY show, or reading Page Six or the Culture section of your favorite publication on the morning of your date can provide relevant but lighthearted go-to material. If all else fails, try a fun question along the lines of ‘If you could travel anywhere tomorrow, where would you go?’ or ‘What’s your go-to karaoke song?’”

 

Drinking on a first date: yes or no?

“There are two camps when it comes to first-date drinking. Lots of people opt for a sober Sunday coffee so they can exit gracefully if it doesn’t feel right. At LastFirst though, we generally feel that the right ambiance sets the stage for chemistry. Dim lights, great music, and yes, drinks! I think that a cocktail or a glass of wine can help let down your guard in a positive way—namely, being less quick to judge and more receptive to new conversation. A drink or two also makes the date more of a special occasion.”

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