Dates Men Love

Whether the guy is shy, outdoorsy, type A, or presents some other challenge, here’s where to go that’ll guarantee you two will bond in no time.

By Celeste Perron

e know: Choosing a destination for a date with a guy can be stressful. You worry that if you pick a plan that makes him uncomfortable, he could clam up or get grouchy and things will take a nosedive from there. But being in charge of the date destination is actually a great opportunity: The right setting could bring out an aspect of his personality you haven’t seen before, while convincing him that you two are a perfect match.

The first step: Think beyond dinner. Many men are made a little uneasy by face-to-face conversation and formal dining with somebody they don’t know all that well, so he might not be at his best in that setting. And regardless, you’re more likely to have a
To make a quiet guy comfortable, choose a setting that provides something to talk about.
memorable bonding experience if you plan something more creative than a meal. Next, choose an activity that’s suited to his personality and interests. We’ve got ideas that will impress the heck out of some of the most common subspecies of the male animal.

For the man of few words...
To make a quiet guy comfortable, choose a setting that provides something to talk about — an art gallery, bowling — so he doesn’t feel pressured to come up with conversation topics and you’re not forced to pepper him with questions. A baseball game is a perfect venue for getting to know such a guy—even if he’s not a diehard fan, he’ll probably have a soft spot for the sport (almost all men seem to), and it’s so easy to follow that it won’t matter if one or both of you aren’t aficionados. Since baseball games are typically long and slow, you can let conversation meander from the action on the diamond to personal topics and back again, a rhythm that takes the spotlight off of him.

One thing to keep in mind, though: Although a guy who’s not a big sports fan will still enjoy a ball game, he probably won’t enjoy it if you happen to know a lot more about baseball than he does and decide to share that knowledge with him. That’s not to say that you should play dumb or play down one of your interests, but if you try to educate him with stats and player bios, he could feel like his masculinity is on trial.

For the type-A guy...
A guy who thrives on competition and accomplishment will have trouble throttling it back enough to enjoy leisurely sunset cocktails or similar activities that ordinary folk find relaxing. Instead, plan a date that allows him to “do” something, but doesn’t require you to bungee-jump into a ravine. A one-night cooking class will keep him busy while giving you time to get to know each other. Even if he’s not a huge foodie, he’ll be keen on the chance to expand upon his areas of mastery (and to engage in an unspoken competition with the other men in the class over who can dice onions fastest).

For an outdoorsy guy...
You know that he’s happiest with fresh air in his lungs, but also know that eating his dirt as you follow him up a mountain trail isn’t the best way to bond. If you want to put off the heavily athletic dates until you’ve been together a bit longer, the trick is to find a plan
A boat ride can be your salvation.
that gets him outdoors without requiring you wear a sports bra or shoes with tread. A boat ride can be your salvation. Chartering a sloop or hopping on a sightseeing boat for a cruise around local waters provides many of the upsides of outdoor adventure—sweeping vistas, wide-open sky, crisp wind against your face—without the dirt and sweat that so many al fresco activities entail. And since there will inevitably be some brisk breezes when you get out on the water, you’ll be forced to huddle close for warmth.

For the alterna-guy...
The typical trappings of romance strike this guy as painfully pedestrian. So skip the charming wine bar you just read about on or a trip to the viewing deck at the top of your local skyscraper. What will warm his heart: a journey to a dimly lit watering hole in a part of town where nobody’s heard of Côtes du Rhone. Look for a spot with unusual ethnic eateries or a neighborhood whose denizens look like extras from an indie film. He prides himself on being on the cutting edge, so if you can introduce him to a gritty place his hipster friends haven’t discovered yet you’ll earn major cred in his eyes.

For the boy who likes toys...
A guy with an intense interest in gear and gadgetry will love a chance to delve deeper into the subject and share it with you. You can’t go wrong with a trip to an automotive museum or classic car show. True, discussing wheel rims and auto bodies may seem to offer few openings for verbal foreplay, but you’ll see a twinkle of delight in his eyes at the suggestion—and hear passion in his voice as he shares his knowledge of all things four-wheeled.

If cars hover way down on your level-of-interest meter, try asking him about the first car he ever drove, the dream car he’d like to drive, his best road trips ever... by the end of the date that passion will no doubt be directed at you, the girl who “gets” him well enough to arrange such a cool date.

Celeste Perron is the author of Playing House: A Starter Guide To Being A Grown-up.
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