Jason from Miamisburg OH asks, “I have been going to the same Sonic Drive-Up Restaurant almost every day for 3 straight weeks. There is an insanely hot roller-skating server working there. What is the best way to ask out a waitress?”
Well Jason, I am glad you asked this question. This is an age-old question that has been around since the first restaurant and the invention of waitresses. Picking up a waitress is one of the most difficult manly-achievements known to man. Waitresses have many natural built-in defense mechanisms against guys like you. You want their number and they want a nice tip.
Most restaurants are managed by male-chauvinistic pigs (I’ve actually never been a restaurant manager, despite what you might think). These managers hire hot young attractive women (when they can) and they train them to flirt. The hotter the waitress, the larger the tips. The more they flirt, the larger the tips. The larger the tips, the less salary the restaurant has to pay her.
The average man has less than a thousand to one odds of scoring her phone number, let alone a single first date. Lucky for you, I am not the average man and I will share with you some of the secrets of picking up a waitress.
So how do you ask out a waitress?
Flirt with them, but flirt with a purpose. You have maybe three or four face-to-face interactions with her to close the deal (even fewer with drive-up service). Tactical Small Talk is your secret to information gathering. Find out if this girl is married or dating someone. Find out what they like to do when they aren’t working. Find out what time they get off work. What time she gets off can be the green-light conversation point to setting up that first meeting outside of the server / patron situation.
Be confident, but not cocky. If you are sheepish and shy, she will see dollar signs in her eyes and start milking you for bigger tips. If you are rude and cocky, she’ll be lucky to talk to you at all other than “What would you like?” If she see’s confidence and charm, she is more likely to look past you as just a customer. This is the target zone…. the More Than Just a Customer zone.
Visit her restaurant frequently, but don’t become a “regular”… You don’t have to always sit in her section, but make a point to say hi to her. Maybe even make some small talk. Remember to smile.
Know her name and make sure she knows yours. First name basis is a way to get you into the More Than Just a Customer zone.
Use other waitresses as ways to gather information on the girl you are trying to date. These servers have to work together and they share stories. Only pursue one waitress at a time.
Tip her well, but don’t over tip. Keep it between 15% and 25%. If you start dropping 40% tips, she’s going to think you are trying to buy her. We’re back to her milking you for tips.
Be forward, but not creepy. If you want to go out with her, tell her that.
Have a plan. When it comes time to asking her out, be detail oriented and make your request authoritative. WRONG WAY – “So, you wanna like maybe go out with me sometime?” Wishy-washy and no details. RIGHT WAY – “I am getting tickets to that . Why don’t I pick you up on Saturday at 6pm. It’ll be fun.” This way you’ve answered the who, what, where, when and why.
Be persistent, but don’t be a pest. Just because she told you no today, doesn’t mean it will be no next week. Try a few times, but again Don’t Be Creepy. If she really isn’t interested in you, the more times you ask, the more she will reach for her can of mace.
If she agrees to go out, follow through with it. Don’t be wishy-washy. Cancel every plan you have to make that date. You might not get a second chance.
This advice applies to waitresses as well as bartenders, even some strippers. There are a few things to watch for when dating a waitress. Waitresses are constantly being hit on by other men; make sure you are OK with that if you want something more long-term. Waitresses often work crappy hours; finding time together may turn out to be a problem. Waitresses will always critique other waitresses when you take them out on dates; just be ready for her catty side. Waitress girlfriends will tip outrageously (40%+) when you run across a good service; make sure you got the cash to support that.
You can have all the good advice in the world and you may still never pick up a waitress. Sometimes you still need the wind to blow the right way or the planets to align. A Ferrari or a large cock doesn’t hurt either. Good luck and happy hunting.
“Ask DaVe” is an advice and Q&A column for all of our readers. I do my best to answer all of your questions. If you don’t know what to do, if you want my opinion on something, if you want to know something about me, or if you just want to know… please write to me at FupDuckTV[at]gmail[dot]com or leave a comment.
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