How To Invite Her On A Date

It’s not just how you ask someone out… it’s also when. Here, strategies from our experts on doing so successfully.

By Phineas Mollod and Jason Tesauro

t’s not just how you ask a woman out; it’s also when. Here, allow us to spell out the implications behind which night you request her company… and how to make things move forward successfully. Let’s go day by day through the week:

The most overlooked, suitable, and safest date night. A relaxed weekend day, Sundates offer both
A good bet: Be super-casual over caffeinated beverages.
parties a chance to avoid the “Sunday night dread” of starting another tough work week. Unlike Friday (PM only) or Saturday (afternoon or PM), you have three time slots to work with — brunch, dinner, evening drink — and the streets are only lightly crowded.

Asker’s benefits: Unlike the glitz of a big Saturday, Sunday is restive, down-to-earth, and thus conducive to discovering the real person within. As the evening wears on, only a feisty soul stays out late on a Sunday. Thus, her willingness to drag into Monday with a sleep deficit signals she considers you quite worthwhile.

Askee’s benefits: AM or PM? A daylight affair means a longer time commitment, but it’s typically more casual. As for PM, the looming Monday morning work excuse is both handy and believable should things not quite click.

The least romantic night of the week and the anti-ideal for pitching first-date woo. On the other hand, after a hot weekend date, calls of “I can’t wait another five business days to see you again” render the Monday evening meet-n-smooch a passionate play.

Asker’s benefits: With many restaurants dark and many people staying home, you’re doubly responsible for bringing turbocharged charisma to a sleepy streetscape. A good bet: Be super-casual over caffeinated beverages.

Askee’s benefits: Unless the date is centered around an event like a concert or trivia night, you’re right to wonder, “Am I getting the crumbs?” While a Monday date may simply signal an uber-busy schedule, the fella asking you out may be a player using this off-night as a casting call for new applicants.

Though lacking the best bands or party scene, there are still ample Tuesday options, especially for something mellower befitting a blind date.

Asker’s benefits: If you’re not a type A, outgoing personality, stay away from
There’s no need for a full costume change from smart work clothes.
weekend nights for early dates since raucous, high-octane evenings don’t showcase a quieter, intellectual sort. Tuesdays are ideal for a casual rendezvous over beer and pizza.

Askee’s benefits: There’s no need for a full costume change from smart work clothes.

People are busy Monday or Tuesday catching up from the weekend or hitting the gym, so Wednesday is often freer and has that “hump day” vibe mid-workweek that can be uplifting.

Asker’s benefits: Things are heating up. If chemistry blooms tonight, look to set up a weekend reprise. Wednesday’s the last day you can ask for a date for the weekend without seeming like the woman you’re asking is an afterthought/last-minute fill-in.

Askee’s benefits: This is a great pick for a first date: Your suitor hasn’t gotten overzealous by asking you out too soon for a weekend date, nor relegated you to the dregs of early week.

Saturday gets all the press, but we think “almost-weekend” Thursday is the best date night. Thursday’s sense of “school-night” intrigue is ripe for spontaneous romance.

Asker’s benefits: She knows you hold her in high esteem. This ought to be as good as any weekend date—and every bit as romantic. Just remember that you’re supposed to turn up for work the next AM.

Askee’s benefits: Wear a weekend-worthy outfit, definitely. It’s a big night—he’s definitely interested. Plus, any wooer who outlines decent Thursday plans is no “weekend warrior” who only goes out Friday and Saturday. He’s ready to court you any night of the week.

Friday night dates are akin to taking off from an aircraft carrier: You’ve got to accelerate quickly and jet into the air. Either transition straight from quittin’ time to happy hour, with slick duds at the ready, or reconvene later, once you’ve recharged, for a late-night munch, followed by music and dancing.

Asker’s benefits: Show her the goods. Long workweeks can sap your date’s stamina, so ready a string of possible activities to keep her highly-interested and mobile, rather than snoozing at the Cineplex by 10 o’clock.

Askee’s benefits: The perfect night to let your friends test-drive a potential flame you’ve been out with once or twice. Say yes to dinner, but make him pick you up on the town where you’re meeting the girls for a drink. If all goes well, he can see you solo next Saturday.

The pressure’s on: There’s a high tide of competition for reservations and the bartender’s attention. To distinguish yourself from the riffraff, show some savvy with the itinerary and the tip jar. Nab a reservation to a hot new restaurant… or show off your smarts with dinner at a little-known gem followed by some music.

Asker’s benefits: For main squeezes only: As the Beach Boys sang, “It’s not right to leave your best girl home on a Saturday night. So if you’re asking her for Saturday, she’s thinking, “Wow, he reeeeally likes me.” If that’s not the message you want to send, tone things down by scheduling a double date and lighten up some of the romantic implications.

Askee’s benefits: Now that you know he’s totally into you, saying yes to a Saturday Night Special is clear sign of reciprocated interest. (If you’re on the fence, suggest an adjournment until early next week.) Good-night kisses are almost surely in the offing.

Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train with his wife and daughter in New York. Jason Tesauro pushes pen and ink by day and leads the lifestyle seminar series by night, ne'er far from his sweetheart and a Brady Bunch houseful 'o tots in Virginia. Together they are the authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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