How To Get A Waitress Go With You


The waitress is a whimsical center of male fantasies – a kind of modern, marginalized, apron-clad goddess of the past couple centuries. Whether she’s the blonde, doe-eyed, Southern-accented sort or the sleek-figured, heavily eye-shadowed silhouette characterized by an ambitious acting career, waitresses seem to embody the best of young(ish) women at work. Unfortunately, a lot of them also seem too preoccupied with their tip jars, vats of coffee and regular customers to spare a moment of flirtation beyond fluttering their lashes as they pass you the bill. How does one lure such a strangely intriguing creature from the corner cafe back to the bedroom? Like everything else that seems impossible and, in actuality, is secretly easy, it’s only a small matter of mind games, great timing and flattering the tip jar.

NOTE: You must identify the caliber of your waitress’ work habits and/or style. Silly as it seems, this is essential to preparing yourself to pounce on her, as various waitresses require various methods of amusement. Second, when entering your waitress’ restaurant, wait a few minutes and stall (i.e. making a pretend phone call, finishing up the front page of the newspaper) as you casually observe what tables your waitress is tending. When you’ve made a good enough guess at her specific section, ask nonchalantly to be seated therein.

The New Girl

If your wanted woman fumbles, nervously glances around, forgets a few drinks and fidgets in the presence of her manager, she’s new (i.e. you have nothing to worry about). New waitresses are thrown into a wildly unorganized world of pain and, therefore, are terribly vulnerable. The best way to win over your new waitress is by offering some comfort in a time when everyone is consumed with condemning her abilities and she herself can’t stop worrying about when or how she will be fired. When she wades over to your table, say “Thank You” always. When she takes you order, smile and say “And please don’t rush, I can see how busy you are by yourself over here.”

Continue to make casual, reassuring comments throughout your meal and soon she’ll be eager to visit, if only to hear what comfort you have to offer next. When at last the bill rolls around, you should say: “You know, I hope I’m not being presumptuous here, but I’d love to sit down to dinner with you sometime soon where someone else is waiting on you.” Waitresses work hard and like very much the idea of restaurants where they don’t work. If you’re too nervous to disrupt her in the middle of her anxious discourse, leave a note with your tips that communicates a similar sentiment (and, of course, your phone number). Remember, new waitresses are most often young, non-locals looking for companionship (meaning – it couldn’t take more than one or two dinners to offer her your company…in bed).

The Sassy Sort

Some waitresses, quite oppositely, are thoughtlessly sure of themselves. If you notice your waitress never misses a mark, constantly manages to run around without appearing disheveled and dazed and memorizes your order without notepad and pen, she’s seasoned. Moreover, if you observe her briskness to be matched by a brushing off of any flirtation or flattery from any customer, she’s sassy. Sassy waitresses are somewhat common and slightly more difficult to sleep with, as they are consistently prepared for piles of flirtatious men. What they’re not prepared for is men who can seemingly read their minds (or at least create the illusion of such). This means flattering her in a creative way. Instead of smiling and asking for frequent refills and ogling her uniform, admire her.

When she next comes to your table, toss out a nonchalant comment in the vain of: “I’m sorry if this sounds bizarre, but you’re an incredibly skilled waitress. I’ve never seen everything go so smoothly. I only say this because it’s super busy and I try to imagine what a mess I’d be.” Here, she’ll probably roll her eyes. Then say something like: “Okay, okay, I’m sorry. I’m sure you’re used to a lot of guys hitting on you. That’s not what I meant. Though, I can see why…” Don’t say anything more – Sassy waitresses appreciate the sultrier, more silent, hard-to-get-type men, so just turn back to your paper or blackberry and pretend she’s already left you. This then means leaving a little note with a big tip, reading: “Okay, so maybe I was hitting on you…while simultaneously being impressed. Still, you should call me.” Women of this type will find such frankness quite adorable and intriguing. After all, they’re used to scoundrels slobbering over them instead of sly lads like yourself.

In Case Of Ignored Motes/Advances

If a note or offer is ignored by a waitress, don’t feel discouraged and determine never to return to the restaurant. On the contrary, make an effort to go back. She’s probably just suspicious of strangers and random notes. If she sees you again and you shamelessly smile, politely nod and request a table in her section, she’ll begin to think you’re a well-intentioned gentleman who simply happens to find her attractive. If you’re the confident sort, who feels he has nothing to lose, say to her “Hello, again,” when she approaches your table. If she doesn’t remember you, remind her, “Oh, I’m just the guy who asked you out and who you probably thought was a creep. Sorry ‘bout that.” Your casualness will make her feel comfortable in letting up a little. If she does remember you, she’ll feel as relaxed as you do. (Translation: be very relaxed). You may actually have more of a chance the second time around, so don’t back down. (NOTE: Another thing not to do: Ask her “When does your shift end, sweetie?” It’s a line she’s heard a thousand times and, moreover, a real lame one).

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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.