Tips For Finding Love And Getting Good Service From The Bartender With Red Hair

The bar was packed and there she was, sitting dominantly in the middle with an empty chair to her left and an empty chair to her right. She was clearly enjoying her wine and an assortment of artisanal cheeses with cured meats. Without even saying a word, she turned around to greet my friend and I and asked if we’d like her to scoot down one so we could sit. And so, the night began.

It was a tight squeeze, but I managed to wedge between my buddy Steve and the lone-diner, Carey. “How’s the evening going?” I asked.

Not bad at all. This is my first break in over two weeks. I’ve got a glass of wine and delicious cheese, what more could a girl want?” she replied.

What is it that you do that enables you to work 20 days straight?” I wondered out loud.

I’m in the food business, working at Florence Restaurant during the day, and at the Blue Light as a bartender during the evenings.” She sliced a piece of cheddar from the cutting board and dropped it in her mouth in between sentences. She continues, “I used to run establishments and make $100,000+ a year, but given the economy, I’m just on call when needed. I love the industry and would rather bartend and waitress than anything else.”

That’ great to hear!” I sincerely replied. Anybody who can stand on their feet for 11 hours a day and work two jobs is a hero! “I’m Sam, and this is my buddy Steve.”

Nice to meet you, I’m Carey. I’m actually going to the Blue Light bar to hang out afterwards. You guys should come, I’ll buy you a round!”

Definitely. But first, we’ve got to ask you about your stories as a bartender. You must have so many!” I reply. Our waiter finally took our order. Two Chimay’s please.


As a relatively attractive woman with red hair, Carey garned a lot of attention, especially from her night job as a bartender at one of the most obnoxious sports bar in town. Carey provided some great insights on everything from getting service to tips on finding love. Here are the highlights:

– When you turn 21, your driver’s license turns horizontal moron, yet the offending kids have no idea. See ya later dumb a**es!

– If you threaten to call the cops on the bartender for confiscating your fake ID, she will laugh in your face and tell you to dial away.

– Don’t wave your dollar bill at the bartender for attention. You will simply her off, because a dollar bill, although better than a piece of dung on the street, is offensive.  Thing strip clubs.  Try a $5 dollar bill instead. If you have a corporate card, even better.

– “Leave it open” is what they want to hear.

– Douche-bags are a dime a dozen. The guys who successfully pick her up, and other women at the bars are simple and straightforward. There’s no need for cheesy pick up lines.

– Writing your name and number on the receipt doesn’t work (shit!). She has a bowl full of these receipts, and she’s never once called a guy back.

* Being comfortable in your skin is very attractive. You can wear jeans and a t-shirt among a crowd of popped colors and Ferragamo shoes. If you are relaxed, you will gain attention.

* Women always become more interested in a man after another woman begins talking to him.

* If you wear three-piece suits, you will attract gold diggers. You are also a douche-bag for wearing a three-piece suit to a bar.

* Respect the establishment. If the dress code is no sandals, get the hell out!

* Of course women are looking for a good time when they are at a bar.  It just might not be with you who doesn’t floss or brush before going out!


If you want to get the ladies or attract the men, get to know the bartender really well at your favorite bar. Being able to get drinks in a crowded bar when you want to is a priceless thing. Your dates will immediately think you are special. Of course, it’s going to cost you a little bit extra for having a great relationship with the bartender.  But isn’t  love worth a $5 tip?

As for Carey, we never ended up meeting her at the next bar. Instead, she just left me a napkin with a restaurant where she works and the three main dishes I must try. Oh yeah, her e-mail and number are on the napkin as well. Cha-ching!

Untemplaters, are you looking for love this Valentine’s week? Do you have any bartender friends who hook you up and make you feel like Norm in Cheers? What are your tips for finding love and getting good service?



The following two tabs change content below.
Sam is the founder of Financial Samurai, America's fastest growing personal finance site. We believe in reaching financial independence sooner, rather than later. Slice through money's mysteries!


  1. Sydney says

    I love the highlights at the bottom! Haha who wears a three piece suit these days? I guess people still do for her to say that. Bartenders must have so many fun stories to hear. They have to put up with a lot though. I only know a friend who went to bartending school, don’t have any friends who are actively bartending now. I do know the hostess and a few waiters at some of my favorite restaurants though which helps a lot in getting a nice table and food quickly.

    My tips for finding love are very simple – don’t be afraid to ask him/her out, don’t waste time trying to be someone you’re not (b/c they’ll see right through you), smile and make jokes to break the ice, know that trust takes time, and don’t be a cheese ball. :) Happy Valentine’s Day!

  2. Tyler S. says

    Doesn’t your license go from vertical to horizontal when you hit 21?

    I am still trying to figure out exactly what “As a relatively attractive woman with red hair,…” means! :)
    Bartenders have seen just about everything and are pros at reading people.. good tips here!

  3. says

    “If you wear three-piece suits, you will attract gold diggers” – the Barney Stinson? Of course, he isn’t exactly interested in cultivating lasting relationships, so to each their own…

    Another trick, if you can swing it, is to show up early enough. That way you can ingratiate yourself by tipping well while you still stick out (less people). Bartenders remember, and they will treat you well the rest of the night. It means less barhopping, but you can let the action come to you!

  4. says

    Whoooh. Good thing I didn’t wear that 3 pice suit. Breaking the ice with new people on Valentine’s day has never been to hard. However, it does help that my birthday is on Valentine’s day, so that is an automatic ice breaker. Great stuff Sam. Is this how true San Franciscans do it? :)

  5. Kris @ simple island living says

    These are great. I used to bartend at my Cheers dive bar before it (sob!) closed, and at a really crazy busy restaurant. I’d like to add…
    If you don’t know what you’re going to get to drink when you get to the front of the line, I don’t care how nice you are or that you’re a regular, I’m going to push you aside and help someone else until you figure it out. Easiest way to figure out who’re inexperienced drinkers.
    I will throw out a regular for bringing in an underage kid. We trust regulars, if you abuse that trust…
    Don’t talk to me when I’m busy. If I know you, I’ll slam out your drink and you wave and say thanks. No chitchat.
    If you’re really nice, I will introduce you to someone you’ll want to know. Really. So if you’re single and looking for love…there’s nothing more fun when it’s slow than setting people up.

    • Sydney says

      I can see how people not knowing what they want when their turn comes must drive bartenders up the wall! When I’m at a crowded bar, I clear out from the counter as soon as my drink comes. I’m not a fan of super busy spots so I prefer to meet up with friends early on in the evening before the peak. Easier to order food/drinks and have a chat with the bartender and waiters.

      • Kris @ Simple Island Living says

        Lol Sam! Of course I got hit on, everyone does. I’ve been dating my husband since I was 19, so I never took any up on their offers. But some of the funnier ones were…
        -the couple that asked me to do a threesome. They were regulars, so it was VERY awkward.
        -the guy who asked to pay me $20 to sit on his lap
        -the guy who told my friend and I he couldn’t decide which one of us he wanted more, so he decided he’d take both and fly us to his private island in the Bahamas.

  6. says

    I was waiting for the payoff at the end of the story – glad it was there.

    If the bar is busy, I order two drinks instead of being the guy desperately trying to get noticed. I try to avoid busy bars anyway, but I’m not in the market for a new woman.

  7. Hunter - Financially Consumed says

    This is cool. I can almost see the dialogue taking place as I read this, picturing what the main players look like. This reminds me of Quentin Tarantino’s style. Fun meeting!

  8. says

    Very smooth Sam, love your work. Love is usually in the last place you expect, as for talking to girls having no other real agenda and listening seemed to work… but that was a while ago for me now 😉

  9. says

    Making pals with the bartender on slow nights is definitely a great way to make an imprint. Applies to restaurants as well. Patronize the place often enough, and you won’t have trouble finding a table quick when you bring that important customer along.

  10. says

    I didn’t even know about vertical licenses until my little brother got his because NJ didn’t implement that until 6 years after I got my license. I’m just happy that I’m done with that whole scene. Oh the stories I could tell!

Leave a Reply

Your email address will not be published. Required fields are marked *