How to plan that date

Guys: How to plan that date

He says: The who, what, and when are easy. But after deciding to ask the who (a woman) out on the what (a date), and after picking the when (next Friday), we’ll have to start talking the where. If we want to show her a good time, we have to show her a good place. It’s a troubling detail, and I’ve often wondered if dating would be easier if it were mandatory to hold all first dates at a prescribed site. Someplace romantic but unthreatening. Like a candle shop. Or a mattress warehouse.

Nonetheless, we have options, and it’s the prudent dater who carefully considers them all before deciding which venue is the most likely to facilitate success in the romance department.

Let’s take a quick tour:

Starbucks. It’s often the first place that comes to mind, as in, “Let’s grab a cup of coffee.” The pros: If the date sours, you can end it without a waiter asking you if you’d like to see a dessert menu. Further, picking Starbucks in particular proves that you’re solvent enough — and employed enough — to drop a healthy ten-note on two flavored waters without batting an eye. It says, “I’m not a barista; on the contrary, baristas do my bidding.” The cons: If the date goes well, you either have to drink 19 cups of caffeine or propose that you continue the date somewhere else (like, say, the Starbucks next door).


An art gallery. Bad move. The only man who can look at a piece of art for more than 13 seconds and not appear to be faking interest is the guy who painted the thing. You don’t want your date to think you’re a total fraud. That comes later.


The zoo. Sure, it’s childish, but childish sometimes works. And meandering among primates provides a nice contrast to your own charms. It says, “Compared to these monkeys, I don’t throw feces.”


Dinner and a movie. Depends on the dinner. And the movie. And the woman. Spago, Being John Malkovich, and the girl you’ve been obsessed with for weeks? Maybe. KFC, Caligula, and the girl who’s been stalking you? Still maybe.


Movie and a dinner. You’ve no doubt committed the first date faux pas of “Let’s just catch a movie before dinner.” The premise is sound: Attend a cultural event and spend the next couple of hours discussing and dissecting it over a fine late-night meal. But inevitably what happens is you show up, say hello, and then spend the next two hours sitting silently next to this perfect stranger jockeying for elbow position while impossibly better-looking people rattle off impossibly better conversation 50 feet tall right before your eyes. Worse, in a mere two hours these matinee idols meet, fall in love, face a daunting romantic obstacle, and fall again back into each other’s arms as they motor off to Martinique. You, however, wrestle over the armrest and then motor off to the Olive Garden.


Your place. If you propose your place for your first date and she accepts, she obviously trusts you more than she should at that point. She’s trouble. Hang up. Run.


Her place. Hard to say. I’ve never mustered the courage to ask a woman out to her place, though I’ve been tempted. Often, when I pick up a woman at her doorstep, I’m amused by the thought that if all goes well — heck, if all goes stupendously — my ultimate goal is merely to return to this very spot… her doorstep. (Often, before I knock on her door, I’ll take a good look around—it’s still daylight, and in the best-case scenario, I’ll be returning to this spot well after the sun has gone down and moonlight will be the only illumination, so now’s my only chance to scope the place out. Case the joint, if you will.)

After all, the intervening hours between the pickup and the drop-off (or hookup) is but an exhausting, puddle-jumping sojourn from romantic restaurant to chichi bar to classic movie theater to late-night coffeehouse—a minimum three-hour tour whose only utility is to prove to my date that I have the capacity to squire her around the town and return her to her home-sweet-home without letting her be pillaged by pirates, kidnapped by renegade truckers, or audited by the IRS. In my hands, she’ll be unscathed by the cruel, cruel world. And as I turn the corner to her apartment building at the end of the night, see the staircase to her front door in the distance, and slow my car to a crawl on the approach, I’m desperate to interpret her subtle sighs and ministrations as a sign that I should stop the car instead of just letting it idle. That I should park, rather than double-park. Because at the end of the day, and the end of the date, if we men have done our jobs, if we’ve performed valiantly, we get to try our luck at a possible goodnight kiss at the place where it all began... her doorstep. The best venue of all.