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So, I am really lucky in that I have a great job at a bar in town, which means I interact with tons of attractive women all the time. I never explicitly hit on my customers — that’s not cool — but when they flirt with me, I find myself completely freezing up! I’m usually a fairly gregarious guy, but I completely lock up when a cutie chats me up. Help?
You certainly sound luckier than most! Maybe you could get this relationship advice columnist on at your bar? I’d love to sling drinks to Louisville’s most attractive. Or maybe just tell me what bar you work at, and I can come hang out? My needs aside, I’m glad that you offered the distinction that you’re not trying to prey on your clientele, but just reciprocate the vibes certain ladies are throwing down. I covered the opposite issue a couple of months ago, when I dedicated a column to service industry professionals dealing with imbibers who don’t realize they’re just being friendly because it’s their job. But what do you do if you’re interested in taking your interactions beyond transactions? Good question.
I mean women are for sure not above flirting with the bartender. I got a bartender’s phone number with my free drink once (Never called him though, because he’d apparently given one of my friend’s the same special offer…). But you have to be careful too. When I lived in Denver, there was a small restaurant I loved taking out of town visitors to. I mean the interior was just gorgeous, the chocolate cake the best I’ve ever had and my fave bartender there was just so damn adorable. But he had the most basic girlfriend ever, and she was straight drama. I’d go in pretty regularly and chat with him, but stopped short of flirting, even after I found out they’d broken up. I was just so hesitant because as a woman, I’m real familiar with what it’s like to be made uncomfortable by someone hitting on you at your job. I didn’t want to hit on him, get shut down and never be able to return — that chocolate cake was that good. So, I tried to be sly. I told another bartender about my crush on him. This backfired because she was into him and, eventually, they got together. I was left wondering if I’d have had a chance if only I’d taken my shot.
For you it’s even riskier, there’s more at stake. What if you misread her flirting and she gets offended and complains? What if she becomes so uncomfortable she never comes back? Or worse, she comes back all the time, and you’re left feeling uncomfortable every time you see her? Or what if you read her correctly, but you two go out on a date and it’s awful? Then what happens the next time she rolls into your bar? What I’m trying to say is that I totally get why you freeze up when it comes to flirting with women at your bar.
The way I see it, you have two choices. One, you could keep letting those fish get away. Feel flattered by their flirting and nothing more. Use it as an ego boost that gives you the courage to approach and flirt with women outside of your place of employment. Two, if you’re determined to pursue these opportunities coming your way on the clock, take it slow. Some folks are just out here flirting with bartenders because they think they’re an easy target and want to feel like they “still got it,” but would probably get all flustered if the bartender flirted back with the intent of going anywhere beyond flirting. So, if your bar isn’t the kind with loud music, I’d focus on having as many rounds of good convo with her as your workload allows. Then at the end, if you’re feeling confident she’s into you, try a line that allows you some room for an out like, “Hey, we have this cool event on Tuesday. It’d be cool to see you again.” *Smile* And you know what smile I’m talking about. If she shows up to the event, it’s probably a good sign you should make your move. You could ask her where she likes to hang out when she’s not at the bar and then express interest, “Oh, I love museums. I haven’t seen that new exhibit at KMAC yet. You?” This leaves the door open for her to say you all should go together, or she could brush the subtle invite off.
Good luck to you, M.A.M. I hope this advice serves you well! •