Over the last few years of waiting tables I’ve witnessed a myriad of guys trying to get with his server/bartender… Some have completely bombed, to the point of getting asked to leave the premise, and some have succeeded and are now married to said server/bartender (let’s be honest: I know the goal isn’t marriage here, but it just proves that one meal with the right moves eventually resulted in the “Game Over” on the relationship ladder)
First of all, know going in, your chances are slim to none… Women in restaurants are relatively used to being hit on, especially if she’s in a bar atmosphere because of the high concentration of drunk men, she has most likely developed a form response to come-ons while the guys just start to blend together. Going out with a complete stranger is frowned upon in girl-world, and most women will find it awkward to get into a one-on-one situation with a guy simply based on the premise that you thought she was hot… not to mention she will be discouraged to pursue something by her co-workers and friends… There’s also the fact, that she’s at work, she has to be there, and has to be nice to you, and you have no idea if she has a boyfriend, another interest, or just won’t ever go out with customers… but here are some ways you can increase the likelihood of a situation working in your favor.
*Ladies: I’m not trying to give away all our secrets, or tell guys how to be manipulative… I’m just trying to give potentially decent/clueless guys a heads-up.
Tip well, like REALLY well: so you chat up your waitress the entire dinner, she’s flirting back, giggling, and paying you obvious attention, so you leave your number, but then leave less than a 20% tip, or even JUST a 20% tip (If someone else is paying, you need to make sure they know this too)… you’ve got absolutely NO shot. This is not about trying to win over a woman with money, it’s about having respect for the societal standards of her occupation. 20% is the national standard right now but going above and beyond is much appreciated. Servers/bartenders not only survive on the tips they make, but are reputably good tippers, so if you don’t tip well, you’re automatically categorized as cheap, and she will not want to go anywhere with you, because she’ll be embarrassed by the tip you leave a fellow industry member. There’s also a mental connotation that hot, confident guys tip well. Even if you don’t get a call, find comfort in the fact that she appreciated your gesture, she talked about you, is flattered, and you made her smile.
Establish a solid connection: Women love to think and occasionally say things to the effect of “Oh my God, we have so much in common” the quicker you find common ground, the better… It can seriously be anything: movies, music, books, hobbies, sports, drinking, favorite places, food, smoking, not smoking, anything… This will increase feelings of familiarity despite being strangers, and by appealing to her interests you’re affirming that she’s not just a pretty face. It will also keep you from blending together with the other guys that are hitting on her. DON’T come on too strong though, this is a fine line to walk because you have to give her inklings that you’re interested, but to keep her intrigued, you have to be relatively discrete. This will ensure that you come across as memorable but not desperate.
Be intensely clever: This isn’t Jersey shore; most women don’t like dumb guys. Originality and self deprecation are key. Play off the things she says, ask her opinion in a table argument, make a bet about something, whatever, just get her involved and coming back to your table for reasons other than her obligatory ones. Also, I think the general public knows that lines are unacceptable in modern wooing efforts, but in case you didn’t know… DON’T USE A LINE… even if you turn it around and make fun of it… just don’t do it.
Pick your Pony: DON’T chat up every girl in the place, let alone the other female servers/bartenders (they’re her friends, and will talk about you at service stations, do walk-bys, give refills, and opinions)… No one wants to go out with the guy that is just going for whatever he can get. It’s ok, and even helps to be charming and flirtatious across the board, women thrive off competition and you become instantaneously more attractive if another woman is into you, but keep your eye on the prize, and somehow make it noticeable that she’s the one you want.
Be good looking: It’s God-given fellas, you either got it or you don’t… If you’ve got it, it’s important that you’re not cocky (there’s a difference between confidence and cockiness), and your physical appearance will initially work in your favor… But for those of you who would never be confused with Bradley Cooper, you better have nailed it beyond a reasonable doubt in every other area of this post, and be so extraordinarily confident and intriguing that your looks cease to matter. Remember: this is not impossible. Ridiculously attractive women are seen with less than average guys constantly. (Heidi Klum/Seal, Paulina Poizkova/Ric Ocasek, Beyonce/Jay-Z, the list could go on forever)
Leave a note: Write it on a napkin, on a receipt copy, coaster, doesn’t matter… and write something clever, or genuine… “You were great, thanks.” is a good default if nothing better comes to mind. If you’re pretty sure you’re going to see the woman again at the bar/restaurant or around town, don’t leave your number, or ask for hers the first time she waits on you. This will leave her wondering and thinking about why you didn’t, and she’ll probably think about you for the rest of the night (this is good for you)… If there’s one thing that heightens a woman’s attraction to a guy, it’s wonderment… We may say that we hate games, and hate guessing, but secretly, we love it. So leave it open-ended, stage another run-in, and go from there… you’re intriguing, not desperate, and most importantly not a stranger anymore, all of which increase your odds.
If for one reason or another you must do the number thing that visit, make the reason very comfortable and non-committal… I don’t think it necessarily matters which way it goes, if she gives you hers, or she gets yours… but make sure the next meeting is a group thing, and encourage the first communication be texting. This takes a lot of pressure/scariness away from the situation.
*Remember when writing the note that if it’s on the merchant copy of a credit card receipt the server doesn’t get to keep it, she has to turn it in to her manager at the end of the night…
Best of luck to you this summer guys :)