6 Ways To Ask Her Out

Wondering how to invite her on a date? Our experts share how to make sure her answer is “Of course!”

By Phineas Mollod and Jason Tesauro

onfidence is one of the touchstones of dating, but the average Joe doesn't need Tony Robbins’ oozing infomercial swagger to be successful on the singles scene. That said, a smooth dating experience starts with the Ask Out, and even if you haven’t tapped into your personal power, you should know how to deliver an assertive, enticing invitation. But beware, the Ask Out is not necessarily a pick-up line. Confused about the difference? Read on.
Demonstrate your desire by explaining why exactly you want to go out.
For the shy, inexperienced, and flustered among us who want to land a date, we now offer up whole phrases to be uttered to any target you fancy.

1. The Classic Close
You may have used all your gold material in chatting up that toothsome barfly, regaling her with humorous stories and sincere flattery, but summon up some final charm for a strong close. Demonstrate your desire by explaining exactly why you want to go out. To the mysterious temptress with tales of international travel: “You’re a captivating globe-trotter... I'd love to see you again after I thumb through an atlas.”

Tailor the Classic Close for your own vernacular and setting:
the show?
link up with
smooches on the town?
connect with
Law & Order reruns on the tube?

2. The “To Be Continued Later, Perhaps?” Request
So things got romantic rather quickly, eh? Following a spontaneous bout of necking on the veranda or party kisses in the coat closet, turn one-time passions into something more by upgrading from the salacious “Your place or mine?” to a chivalrous “This is really fun, but I think there's more. Let's see if we’re as adept at dinner conversation as we are at kissing.” You've already consummated interest; why not lobby for a first date even if it’s after the fact? Of course, this can backfire if wild-night spontaneity fades faster than lip gloss marks across your cheek, but hey, strike while the breath is still hot.

3. The Public Ask Out
Unlike the privacy of a one-on-one meeting, you may have to navigate around relatives or colleagues who might butt in while you're making your move. Now, a blatant Ask Out might be a little gauche or on-the-spot before too many witnesses. So once initial interest is confirmed with innuendo and eye contact, subtlety is the cool play. Couch your words within a seemingly innocuous question: "Let’s exchange email addresses so I can get that link to that ice-fishing website you mentioned [wink]." In short, be discreet and keep it PG-13 lest Big Brother (especially hers) is watching.

4. The Grandiloquent Gesture
Sometimes a little showmanship is needed to close the deal, especially when there’s other competition beating around the bush like so many suitors chatting up Penelope while Odysseus was boating around the Ionian Sea. Akin to a superstar free agent
Allow the conversation to reach a fever pitch of fun before setting a plan.
wooed by several teams, a sassy gal might have many feelers out there, so be prepared to up the stakes with a compelling offer and a signing bonus. This is no time for a middling pitch like: “We should catch a flick one night.” Instead, be assertive and do it with flair that ensures a yes. Rather than the typical “ask now, make a plan later” routine, build into the Ask Out a preview of the date: “Pick an afternoon… I’ll meet you outside your office with bubbly and my crème brulée torch. If we kiss, I’ll even share the recipe.”

5. The On-the-Horn Ask
For most online daters, the telephone is a useful middle step between email and face-to-face. Despite your perfectly-coiffed profile pics and stream of electronic prose, nothing is certain, and you need to resell yourself over the phone. As for blind dates, once you’ve landed digits, it’s assumed you’ll use them to ask for a date. Yet, in lieu of jumping right in with a terse, “I’ll see you at eight,” re-engage and allow the conversation to reach a fever pitch of fun before setting a plan: “I was laughing so much I almost forgot why I called... let's go out Friday" Before dialing, be ready for voicemail with a tempting plan of action. A date spelled out by telephone is an easy way to gauge interest: No call back = no interest; immediate call back = let’s go.

6. The Spontaneous Rendezvous Request
On the street, at the supermarket, in the coin-op laundromat… you meet someone at a venue that isn't usually built for romance. Unlike a traditional date request, where several days notice is offered, this kind of flirtation requires a way station before gambling on the four-hour commitment that is dinner and a movie. "You want to go get a cup of coffee" is the pinnacle; if it's post-midnight, try: "Would you like to join me for late-night omelet/danish at the diner?" At the dog park: "My hound is too shy to ask your pup for a date, so I’ll speak up instead. Care to grab a biscuit and a latté?" Put that chemistry to the test right now. Then, while flirting over mochas, ask her out and make plans to meet again... this time on purpose.

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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