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How to sit at the bar alone and actually meet people instead of just staring at your phone the whole time

A guide for the socially awkward.

Dec 8, 2025
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As you may have heard, the hottest dating advice of the moment is to go out alone and interact with strangers. The trend that made the rounds on TikTok last month as “Sit at the Bar September” actually kicked off earlier this year when comedian and podcast host Jared Freid introduced a “summer dating challenge” on the Betches U Up? podcast. The premise is simple: Get off the dating apps, go out alone and sit at the bar by yourself, put your damn phone away, and talk to people.

Sounds easy enough, I know! But unfortunately, for a member of the socially awkward community such as myself, you might as well be telling me to meet men by running headfirst into a burning building. As a woman with naturally strange and offputting vibes, you could say I’m someone who’s been known to struggle with “making friends” and “social interaction” and “not automatically assuming everyone hates me and thinks I’m a loser until proven otherwise.” When Olivia Rodrigo said, “Searchin’ ‘how to start a conversation’ on a website,” I felt that.

In short, I’m afraid I am the exact kind of person dating apps were invented for: those who fear rejection and cling to the safety net of already knowing someone is into you before you ever have to say actual words to them. But while the apps did well by me in their heyday, I, too, am now over it and would prefer to meet people in real life.

As someone who loves both drinking and being alone, the idea of going out and sitting at a bar by myself sounds like a great time—it’s just the “actually talking to other people” part that gives me pause. Like, I’m pretty sure I would just spend the entire time with my eyes glued to my social anxiety support phone, quietly going into fight or flight at the thought of someone initiating conversation with me even though that’s literally the whole point, and then wind up downing three martinis and blacking out on a weeknight for no reason.

That said! I absolutely do see the value of this dating strategy! So I reached out to some people who are much less socially inept than myself for their tips on how to do the seemingly simple but also somehow seemingly impossible: go out alone and actually meet people. Here are their expert tips on how to simply have a normal human interaction.

Expect (and Accept) Rejection

While the goal of this “sit at the bar”–style dating advice is ostensibly to meet potential romantic partners, the reality is that bumping into the love of your life at the bar is…not particularly likely—and that’s okay! As Freid, the comedian and U Up? podcast cohost, explains, dating apps are very much a goal-oriented approach to dating designed to help you meet people without the risk of rejection. But if you want to get off the apps, go out, and meet people in real life, you’re going to have to accept that rejection is part of the game.

“My advice is, don’t get down on yourself,” says Freid.

You might strike out! You might feel awkward! You might try to start a conversation with someone, get turned down, and feel bad about it! These things are all not just okay but a completely normal part of having real-world human experiences! The apps have just conditioned us to be hyper-sensitive to rejection because they’ve enabled us to avoid it.

“You’re going to get more on a dating app—more matches, more conversations, more dopamine,” says Freid. “The in-person meeting will be more fruitful, but it’s going to happen less often.” Essentially, it’s a game of “more failure but better return.”

Reframe Your Expectations

Again, sitting at a bar by yourself is not some magic trick that will automatically attract hordes of suitors. If your goal is to leave with a date, you’re more likely to wind up disappointed than not.

“Reframe what ‘success’ means, because going out alone to meet people is not about meeting your future partner—it’s about enjoying yourself and practicing being comfortable in your own company,” says therapist and dating expert Michelle Herzog. “If you go out with the singular goal of finding someone, you’ll give off desperate energy and set yourself up for disappointment.”

This means being open to talking to anybody—not just potential romantic prospects, says Freid. Not only because you’ll naturally seem more attractive if you’re actually engaging with people regardless of their relationship status instead of hyper-focusing on finding someone to flirt with but also because you never know where a connection might lead. A new friend could turn out to be the person who sets you up on a date with one of their single friends or invites you to a party where you meet someone new. The goal is to have fun and connect with people, not just people you want to date.

Put Your Phone Away

This is a pretty core tenet of the original U Up? summer dating challenge—and while it may seem terrifying, putting your phone away is 100 percent necessary if you want to do it right.

“Our phones and headphones have become defense mechanisms and signal ‘Do not approach or look at me’ to other people,” says Take It From a Woman editor Logan Mahan. “When we’re feeling slightly awkward or uncomfortable—especially about being alone in a public place—we check the time or absentmindedly open random apps to look busy. I think we’re all guilty of it.”

But if you want to meet people instead of just staring at your phone feeling awkward, you’re going to have to, you know, resist the urge to stare at your phone when you’re feeling awkward. Unfair, I know.

If you still need a buffer between you and the awkwardness, Mahan suggests bringing a book, adding that this could even get the attention of someone who might strike up a conversation about your reading material. Still, you’re going to need to resist the urge to rely too much on your social anxiety support prop, as burying your nose in a book and refusing to look at anything else gives pretty much the same “don’t talk to me” vibes as being glued to your phone but with an extra layer of pretentiousness.

Talk to People!

Okay, now for the tricky part: actually interacting with people.

“Be open, be personable, and don’t be afraid to initiate conversation,” says Mahan.

Remember: A bar is an inherently social environment. Not only is it totally normal to strike up a conversation with a stranger in this context, but as Mahan points out, the environment itself probably gives you plenty of things to talk about: “If I overhear a group of guys talking about a sports team—especially one I don’t like—I have no problem inserting my opinion or cracking a joke. If I like a man’s jacket, I’ll tell him and ask him where it’s from. If he’s drinking a cocktail, I’ll ask him if it’s good or if I should order one for myself.”

In short, “Just be willing to yap,” says Mahan.

Eavesdrop

Fun fact: Eavesdropping is only rude if you don’t make your presence known. Otherwise, it’s just listening to what other people are saying and responding, which is also known as making conversation.

“Eavesdropping on the conversations happening around you is an easy way to introduce yourself and start up a conversation with someone,” says Mahan. Obviously, you need to read the room and avoid barging into someone’s intimate convo. “But if you hear someone discussing a new album or film or a sports team you have opinions on, wait for a slight lull in the conversation and say something like, ‘Sorry, I don’t mean to eavesdrop, but I couldn’t help but overhear…,’” Mahan suggests. “Nine out of 10 times I’ve done this, people are very receptive and happy to chat.”

Talk to the Bartender

The bartender is basically your built-in social anxiety support friend. Not only do bartenders tend to be naturally social people, but chatting with customers is kind of part of the gig. If you’re too nervous to start a conversation with a fellow patron, try easing into things by chatting with someone who’s essentially getting paid to be there and make you feel welcome. (Assuming they’re not busy, of course. Again, reading the room is key!)

Not to mention, “Your bartenders might be familiar with that hot guy who’s sitting at the bar next to you,” says Mahan. “If you’re talking to the bartender, they might loop other patrons into the conversation.”

Become a Regular

Speaking of befriending the bartender, becoming a regular at a favorite spot is a great way to naturally get to know the staff and other regulars, says therapist and dating coach Kelsey Wonderlin, adding that it may take a few tries to find a place that you like. Being in an environment where you feel welcome and comfortable will obviously help put you at ease, and going to the same place multiple times will allow you to form connections gradually over time.

And when it comes to trying out a new spot, Freid recommends being intentional and doing your research. Instead of just popping into any random bar, pick a place that has something specific you want to check out, whether it’s a signature cocktail, a burger everybody raves about, or some other unique feature that catches your attention. “If you go to a place that you’ve read about and someone approaches you, now you have a thing to talk about,” says Freid.

“Timing matters too,” adds Herzog. “Try happy hour or weeknight evenings when the pace is slower rather than packed Saturday nights.” You obviously don’t want to go somewhere that’s totally dead, but a super-loud, crowded hot spot is probably not going to be conducive to actually getting to know people.

Don’t Be Afraid to Approach People (Especially Men)

As a woman who dates men, I know many of us (myself included) prefer to let the guys make the first move. But if you’re waiting around for a man to chat you up, you’re probably just wasting your own time.

“Many confident, awesome guys are afraid to approach women because they don’t want to be perceived as creepy,” says matchmaker and dating coach Blaine Anderson, founder of Dating by Blaine. “Stop waiting and take the lead. Men love being approached. Literally 100 percent of single men wish women initiated conversations with them more.”

While I cannot verify that exact statistic, Freid confirms that men do, in fact, want to be approached: “Yes, men love when women talk to them.”

There you have it!

It’s Okay to Have a Go-To Opening Line

Ideally, you’ll be able to strike up a conversation organically, but it’s totally fine to have a go-to icebreaker on file if you need it. Freid’s suggestion? “Hey, I love your shoes.”

“That is the best opening line,” he tells Cosmo. “It’s not sexual, it’s not anything—just an easy thing to remember to open someone up to a conversation.”

Herzog also suggests asking someone for a small recommendation, like what drink they usually order or if they’ve tried the food. “It is low-pressure, gives the other person an easy out if they’re not interested, and opens the door naturally.”

The idea is really just to have something chill—not too aggressive, niche, or overtly flirtatious—to break the ice.

“The hardest part is taking the first step, so don’t sweat coming up with the perfect line,” says Anderson. “You can literally say, ‘I don’t think we’ve met—I’m [insert name].’ If you’re feeling bold, you could say, ‘I think you’re cute, so I wanted to say hi.’ You can say almost anything you want.”

Be Approachable

While making the first move instead of waiting to be approached is obviously encouraged, making yourself seem approachable is also important.

“Body language is everything. If you’re hunched over your phone or have your arms crossed, you’re essentially wearing a ‘do not disturb’ sign,” says Herzog. “Instead, sit or stand facing outward rather than tucking into a corner, make occasional eye contact with people around you, and smile when something genuinely amuses you.”

Herzog also recommends wearing or bringing some kind of conversation piece, “like a unique piece of jewelry or clothing, an interesting book cover, or a sports team hat. These ‘social hooks’ give people an easy, nonthreatening opportunity to start talking.”

And when in doubt, remember that sometimes eye contact speaks louder than words.

“Make eye contact with someone across the room,” says Mahan. “Let them know you’re there, you’ve noticed them, and you’re open to a conversation—and let the universe take it from there.”

Credit: Cosmopolitan

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