Bartenders are like the unseen, untapped fountain of wisdom. We’re often present during your most vulnerable moments, both painful and celebratory. This makes us privy to some of your most personal activities—especially dating.
As a former bartender, I’ve witnessed it all: awkward flirtations, unwanted advances, and disastrous first-date dialogues that leave me thinking, “Why’d you say that?” while I’m cleaning glasses.
Though I’m no relationship expert, my time behind the bar has given me some (often unsolicited) insights into what works and what doesn’t. From my vantage point, having seen dates crash and burn countless times, I can offer a few recommendations.
1) Don’t ask us to be your wingman.
No matter how well we get along, don’t ask us to help you pick someone up. It’s unprofessional and morally wrong. Besides, we probably don’t know you well enough to do this anyway. Our job is to be friendly, not part of your friend group. Save that job for them.
2) Don’t ply your date with drinks.
If you keep asking her if she wants another drink, it’ll seem suspicious. Even if you’re just being considerate, she may misinterpret it. You don’t want her to think you’re trying to get her drunk. If she wants another drink, she’ll ask for it or order it herself.
3) Avoid lulls in conversation.
The bar atmosphere might seem lively enough to mask awkward silences, but it won’t. On a first date, you definitely want to avoid that awkwardness. Come prepared with conversation starters. If things do get quiet, take the opportunity to suggest a new activity. Ask her if she’d like to go for a walk.
4) Pick-up lines don’t work.
We’re not just talking about the cheesy “Did it hurt when you fell from Heaven?” pick-up lines. Any overused line will fall flat. If you see someone you’re interested in, just be real. Approach her, start a conversation, give a small compliment, and read her body language. That’s your best guide.
5) Neither does cockiness.
Bragging about how much you can drink, how tight you are with the bartender, or showing off your car are all ways to turn her off. Sometimes, liquid courage can make even the most grounded guys overly cocky. Resist that temptation.
6) There’s a right way to buy her a drink.
Do not order a drink and then hand it directly to her. Women are more cautious about accepting drinks from strangers. If you want to buy her a drink, there are two options: You can offer to buy it and walk with her to the bar, or you can ask the bartender to relay the message.
7) Pay attention to drinking habits.
Your date’s drinking habits are important—and so are yours. Don’t keep knocking back drinks, especially on a first date. It’ll give her the impression that you need alcohol to have a good time. Similarly, if she’s drinking too much and getting sloppy, it’s a sign that things may not work out.
8) Don’t bring us into the conversation.
If you’re struggling to keep the conversation going, don’t drag us into it. This makes the situation awkward for everyone. It will make your date feel unimportant and forgotten. If you attempt to bring us into the conversation with “Can you tell my date…” while she’s right there, just don’t.
9) Avoid trite departure phrases.
“Do you want to get out of here?” or “Let’s go somewhere quiet to talk” are big red flags. Even if you mean well, this kind of language feels inauthentic and suspicious. Your date will likely pick up on it, and it won’t make a good impression.
10) Don’t bring all your dates to the same bar.
We’ll recognize you, especially if you’re a regular. And that’s not going to leave a favorable impression on your date. You might hear “So, you come here often?” and, trust me, it’s not just a casual observation—it’s a judgment. Even if you frequent the place twice, don’t overstate your familiarity with it. This just carries negative connotations on a first date.
Bonus Tip: Keep It Real
Authenticity is key. Something about bars and drinking tends to turn people into more confident but sometimes exaggerated versions of themselves. If the bartender can tell, your date will too.
As bartenders, we’ve seen people through some of their toughest times—breakups, depression, and even grief. But we’ve also seen moments of pure joy and happiness. Our front-row seat to these human experiences makes us a valuable source of observation. So, next time you’re at a bar and someone catches your eye, take these tips to heart before you make your move.