Putting the Best Foot Forward
Flirt subtly. Waitresses deal with forward men every month, every week, and maybe every shift. Being too eager, too bold, or too aggressive in your approach can cause her to raise her defenses before you’ve even made a play. “He’s just another one of THOSE guys,” she may say to herself. This will doom your goal. A boor will say something like, “Hey, what time does your shift end?” Not only is this a terrible line but it is also creepy, making it seem as though you will be waiting for her at closing time. Don’t be so transparent, and don’t be creepy. Instead, try engaging her in conversation, i.e. “This is my first time here. Wow, are you always so busy on Tuesdays?”
Be polite. Like with flirting, you should be a gentleman and on your best behavior. Make it clear that you are nice, respectful, and thoughtful – again, not some creep. Employ the usual trappings of politeness that you use in other social situations. Say please and thank you. A waitress is serving you, but she is still a person and should be treated like it. This is just normal kindness. Don’t call her sweetheart or any other “pet name.” It is condescending. Also, don’t stare at her. She may well be very pretty, but you will probably make her uncomfortable. Avoid complaining about the restaurant. Your waitress did not write the menu, set the prices, design the décore. Nor does she control how busy the establishment is. Complaining will only put her off. You might try empathizing with her, though. For example, if the restaurant is annoyingly busy, express your solidarity, i.e. “It sure is busy tonight. They should really give you more help with the tables.”
Order what she recommends. Your waitress knows the menu like the back of her hand. She knows what’s good, what’s so-so, and what ends up in the garbage. Ask her for recommendations. She’ll notice and point you toward a good meal. It shows a level of trust and turns the conversation to her. Conversely, don’t order something that is not on the menu or ask her to make substitutions. This makes her job harder and will only serve as an annoyance.
Talk about something other than food. She has been talking about food the whole day. Turn the conversation to something more interesting, whether about you or her. Try to make yourself seem genuinely interesting. No long conversations about who the restaurant’s beef supplier is, or how much they pay for vodka wholesale. Talk about yourself a bit, or at least hint at it. Waitresses are hit on a lot, and while they're always friendly about it, they probably will turn you down if they don't know you well. At the same time, turn the conversation to her. Talking only about yourself might come off as self-absorbed. Empathic people ask questions and listen to others.
Tip well. Keep in mind that tips make up about 85% of a waitress’ total wages. Tipping is not just polite, but says that you are well-mannered as well as confident, friendly, and interested. Tip what you can afford, but don’t be stingy. You will leave a better impression if you err on the side of generosity. You may remember when 15% was pretty standard for good service. Those days are long gone. Nowadays the standard tip is closer to 20%. Aim for 20% or even 25% for the best effect.
Avoiding Common Mistakes
Don’t monopolize her attention. Remember that your waitress is working and earning a living. She has other tables to serve and other demands on her time. If you try to get her attention too often, she’ll quickly get annoyed. Remember that she may be very busy. It might even be kind to acknowledge it, i.e. “I don’t want to keep you here talking too long. I can see that you have a lot of work to do!” Keep in mind as well that, if you monopolize her time, she might get in trouble with her employers.
Avoid sexual advances. Nothing – but nothing – will doom your efforts to catch your waitress’ fancy than suggestive or crude overtures. Remember to put your best foot forward and be polite, ever the gentleman. You are in a restaurant, not a night club or frat house. It is never OK to touch or make unwanted advances. This applies not just to your waitress but any woman. No sexual comments, gestures, or banter. Alcohol may lower your inhibitions and lead you to say things you’ll regret. Be careful not to carry on your flirting if you’ve been drinking too much. As in all social situations, if she asks you to stop something, stop it.
Don’t overstay your welcome. Your first thought might be that the waitress will have more time and be more open to accepting a date if you wait until she stops working. This first thought is wrong. Instead, it looks creepy. Know when to pick your spot and leave. Very probably your waitress doesn’t want to join you for a drink or coffee immediately after her shift. More likely she wants to go home. You’d be better served by deciding to ask her, making your play, and getting on with your night. If the waitress thinks that you are interested, your sticking around for hours will become a major distraction and annoyance to her.
Don’t necessarily ask the first time. If you have struck up an interesting conversation with your waitress and feel a bond, you needn’t act on your first impulse. Take your time. Try stopping in once in a while if the restaurant is conveniently located. Build up a mutual recognition. It may be a good sign if she notices when you stop in or says hello. While being a regular is OK, avoid frequenting the restaurant too often lest you seem like a stalker. If you always eat at the same table and always smile at her, she may be creeped out.
Making Your Move
Build up a rapport. Using the techniques we’ve discussed, try to get to know the waitress a bit. Talk over the course of several meals or drinks, if possible, and learn about her while subtly introducing yourself. This way your request for a date will not seem like it’s coming from a complete stranger. Try to sit at one of the tables she is serving. Take note of any giveaways that she is unavailable, like a ring on her left hand.
Leave a note on a napkin. One way to ask her out without the embarrassment of a possible rejection is to leave a note on one side of a napkin. After paying, jot down your name and number and then leave. If she’s interested, she’ll respond. Notes also leave the matter entirely in her hand and spares her from feeling pressure or having to make a hasty decision. Be short and to the point, i.e. “You seem like a thoughtful person that I’d interested to know better. Coffee sometime?” End with your name and number. Insert a nice tip into the fold of a napkin, with the money is sticking out. Make sure that she will notice the tip or someone else could pick it up Use a clean napkin if you decide on this route.
Leave a note in the check presenter. In this variant, leave your note inside of the check presenter with your payment and tip. Go with the same approach, including a short offer to take her out and your name and number. Don’t stick around, as it will only make her uncomfortable. Unlike a napkin, the check presenter should be fairly secure and discreet. In many restaurants, there is an unspoken rule that servers only touch check presenters from their table. If there is room, write the message directly onto the receipt. If not, use a napkin in a pinch. Aim for a kind and no-pressure request, i.e. “To my charming waitress: pardon my forwardness, but I’d love to take you out. (Insert phone number). Call me sometime. I’d love to hear from you.
Hand her a note with your tip or receipt. This gambit involves your passing the note to the waitress directly as you leave the restaurant. Bold, but sure to get her attention. Tuck your tip inside of folded piece of paper with your note. Write something like, “(Your name and number) Dinner sometime? Call me anytime. I’d love to hear from you!” Hand her the note as you walk to the door, saying, “This is for you.”
Accept a rejection. Your move may well not work out. Your waitress might have just been friendly, or perhaps she is married or involved with someone else. In any case, do not push it any further. Accept the rejection and move on. The beauty of the note request is its discreetness and also lack of pressure. If you asked her out on a note, you’ll know she is interested or not by her response. The ball is in her court. Don’t be discouraged if you’ve tried all of the above and she doesn’t call. At least you tried – many men would not!
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