The Dos and Don'ts of Going on a First Date

Updated 05/06/19

First dates can be risky business. A Molotov cocktail of both uncertainty and promise, evaluating the potential of a relationship upon a single encounter might feel exciting or mind-boggling, depending on one’s perspective. We decided to let a few men weigh in on the best and worst moves they’ve encountered via meet-cute.

Whether or not you take their advice is up to you. So if you’ve found certain approaches or techniques that work well for you, then by all means, stick to those best practices. Regardless, it’s certainly interesting to at least hear them out. Keep scrolling to find out what they had to say about charming your way through your first date and night out.

Do Put Your Phone Away

We live in a world oversaturated with opportunities to connect with everything and everyone at any given moment. Suppress the urge to Instagram, text, or reach out to your network, and instead, go off-grid. 

“Live dangerously. Throw your phone in airplane mode.” — Tyler, 26

“On my first date with my fiancée, I went to the bathroom halfway through our dinner. When I returned, my date was sitting at the table. Doing what? Well, just looking around. It shows confidence. It’s sexy. I told her so on the spot.” — Reid, 35

Mansur Gavriel Calf Leather Elegant Bag $825

If it’s hard for you to stash your cell phone away for the night, this elegant and stylish top-handle purse should make things easier since you’ll know it’s in good hands.

Don't Talk About Previous Relationships

Universally, every guy we polled gave the same note over and over. 

“Don’t bring up past relationships—good or bad!” — Ben, 24

Ferm Living Candle Extinguisher $37

Nothing will kill a budding romance like bringing up your exes on the first date. You may as well blow out the candles and call it a night.

Do Wear Cool Shoes

When deciding what to wear, steer clear of anything too fashion-forward or flashy. Save the harem pants and power shoulders for girls’ night. Fancy footwear, however, got the green light from the guys. 

“Do go sexy with the shoe game. Don’t wear sequins.” — Devin, 31

Oscar Tiye Giorgia Textured-Lamé Boots $685

Nothing says you’re ready for a good time like these disco-ready boots. 

Do Ask Thoughtful Questions

The art of conversation involves mindfulness and listening. While it’s preferable to steer clear of a super-heavy line of inquiry, lest the encounter start to feel more like an interview than a budding romance, asking thoughtful questions is a must. 

“Ask questions and be genuinely interested in the answers. Then use said answers to keep the conversation going.” — Reid, 35

BZippy Cone Vase Evelyn $222

Assuming your date brings you flowers, have a cool vase to stick them in while you enjoy an evening of conversation. 

Do Mention Dietary Restrictions

Fully disclose any dietary restraints, from food allergies to vegetarianism, in advance. If you’re a picky eater, maybe even offer to choose the restaurant. 

“If you have dietary restrictions, let me know before I take you somewhere. Unforeseen variables throw off your game. If you’re vegan, we don’t want to end up at a steakhouse.” — Will, 29

Joe Warwick Where Chefs Eat $16

This book will give you plenty of restaurant options, no matter your culinary inclinations.

Don't Force The Chemistry

Every date carries with it the intangibles of physical attraction and an easy rapport. Who can say what unique alchemy determines chemistry? The men we spoke to emphasized the importance of being open and not settling. 

“Trust your instincts. There should be a natural spark. Don’t negotiate what you’re looking for just because you want it to work.” — Sean, 33

Fredericks & Mae Fireplace Matches $12

You can’t force chemistry, but you can strike a literal spark with these cool matches.

Do Break The Touch Barrier Yourself

That first moment of physical contact can be awkward to maneuver. If you’re feeling it, instead of waiting for him to make the first move, go ahead and break the barrier yourself. Take matters into your own hands—literally.

“A lot of nice guys are shy. They may not be skilled in flirting. Touch his arm—anything to give him a signal he has permission to go ahead.” — Sean, 33

Creatures of Comfort Crescent Moon Bottle Opener $63

If you happen to be tailgating or enjoying a beautiful view outside on your first date, keep this chic bottle opener handy.

Have you learned the dos and don’ts of first dates the hard way? Share your funny anecdotes and sage advice with us in the comment section below.

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