8 Common Flirting And First Date Mistakes, According To Bartenders

From awkward flirting mishaps to first date mistakes to avoid, bartenders have seen it all. Before dating apps became the norm, many people made it a point to go out to bars in order to meet new people. Trying to meet someone that way can have its ups and downs, but if you're looking to meet people in more "traditional" ways, Christina Oswald, the bartender at Mark Ridley’s Comedy Castle in Royal Oak, MI says it's still very effective.

"You have the opportunity to make an instant connection rather than days of messaging on a dating app just to have them flake on you," Oswald says. "On the other hand, there is the painful fear of being rejected right to your face. I find that this fear is real in a woman’s mind, but in 11 years of bartending, I have only seen this scenario play out once or twice."

If you're going to flirt with someone you meet at a bar, Oswald says there are "types" you should watch out for like the one who instantly buys you a drink the moment you sit down. "This person typically lingers at the bar just waiting for [a person] to walk up," she says. "It's a numbers game for them and they know that this kind of gesture will suck people in."

Chances are, they played the same old game last weekend and the weekend before. It's great if you're looking for a one-night stand, but not so great if you're looking for "The One." "If you have not exchanged friendly conversation with someone before they buy you a drink, question their motives," Oswald says.

Whether you're at a bar to meet someone new or you're there for a first date, these are some common mistakes to avoid, according to bartenders.

1Bragging A Little Too Much

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"I’d say the biggest first date mistakes I see people making are bragging about themselves or endlessly talking, not giving their date a chance to interject," Chris Resnick, lead bartender at Minnow Bar in Miami Beach, tells Bustle.

When it comes to talking too much, Resnick says it often goes south when one of the people on the date inevitably starts talking about their ex thanks to the alcohol. "Keep it light and stay calm," Resnick says. "Don’t get too heavy on the first date. There might not be a second one."

2Trying To Impress Your Date With Alcohol

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Speaking of alcohol, you might not want to over do it. "I’ve witnessed people trying to over impress their date and end up drinking too much," Giorgio Casalinuovo from La Moderna in Miami Beach’s Sunset Harbour tells Bustle. "You don’t want to be drunk on your first date. Stick to one spirit (suggestion: a Negroni is a classic drink you can’t go wrong with) and have a few cocktails." Sip casually while getting to know one another and make sure to order something to eat so you’re not drinking on an empty stomach. "Pace yourself," Casalinuovo says. "This isn’t a race."

For an expert tip, go to a bar that you frequent often where the bartender knows your name. "We always hook it up for our loyal customers," he says. "You'll be able to treat your date to a VIP experience without the price tag." Definitely keep that in mind!

3Assuming You Know What They Like To Eat Or Drink


Even if you go to a bar all the time and you seem to know what's good and what's not, don't make assumptions. Just because some people think a certain drink is really good, it doesn't mean your date will. Besides, if you order for them in order to impress them, you might miss an opportunity to get to know them.

"My best advice is to ask the other person what they like to eat and drink," Adam R. Seger, CCP, Chef Bartender and Corporate Sommelier, tells Bustle. "Depending on how thorough they are, follow-up on what their best food memory is."

According to Seger, people love to talk about themselves. "They will actually think that you are more interesting when they actually talk about themselves. You will also learn a great deal about their passions, upbringing and how they grew up. And then you can order appropriate food and drink that will open up more real conversation."

4Ordering Something Just To Impress Your Date

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When it comes to ordering, don’t order to impress someone, order something you know instead. "First dates are all about making a great impression and you want to win over your potential new partner," Jason, part owner of Taylor Made Bartender services, tells Bustle. Don’t order something you’ve heard from your favorite song or you've seen on Instagram without knowing what it's about. "Stick to what you like and may know [already and] order your drink with confidence ensuring your potential partner you have some knowledge of what your drinking," he says.

5Failing To Think About Where And How You're Sitting


"Think about where and how you are sitting," Oswald says. "I see so many dates that 'belly up' to the bar, facing me (or worse TVs) and not their dates. This creates a disconnect." Her advice is to try to find the corner of the bar or a high top table where you can face each other. If that isn't an option, make an effort to position yourself toward your date.

As a bonus tip, "If you know your date is a sports fan, try to choose a bar without TVs," she says. This way your date will not potentially get distracted.

6Coming Off As Unapproachable

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If you're not on a first date, but you went to the bar with the intention of meeting someone new, try to use body language that helps you appear approachable. Oswald says this can include physically showing someone you're game to chat, which could mean throwing them a smile, if you're feeling it. If you're there with a friend, try not to sit too close together, so that someone new doesn't feel you are already engaged in a conversation. Or better yet, go up to an interesting person yourself, and start a conversation.

7Staying In A Conversation That's Going Nowhere

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If you're talking to someone after 10 minutes and you're just not feeling it, don't stay. "Don’t be afraid to end a conversation that is going nowhere," Oswald says. "Don't worry. They'll find someone else to talk to. If they're persistent and won’t leave you alone, call in reinforcements. Tell the bartender — we take great enjoyment in telling creeps to buzz off."

8Touching The Garnish On Your Drink

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"I think everyone makes mistakes on the first date but occasionally I see some that are extra special," Gregory Westcott, Bar Manager at LA's hotspot, Hinoki & the Bird, tells Bustle. "Spicy food and drinks are on almost every cocktail menu. Don’t touch any chili peppers that are used as a garnish! The oils will stay on your hands for a long time and if you use the bathroom, or things get sexy, then you will feel the burn!" Clearly, bartenders have seen it all.

Lastly, if you want to flirt with the bartender, Amy DeLee from San Diego’s Jalisco Cantina tells Bustle, "Leaving the bartender your phone number while tipping under 20 percent is a fatal faux pas." So be sure to treat the bartender well while slipping them your digits.

While meeting someone out is not always easy, keep these bartenders' tips in mind and you may have more success the next time you try the bar approach.