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Ali Jackson had been single for about four years, and like so many women, felt burned out on dating apps. Swiping had become a monotonous routine, something to do when she was bored. So Jackson decided to delete the apps and try something novel: Meet people in person.
In October, she made a commitment to attend two social events a month where she didn’t know many people. Initially, Jackson signed up for singles mixers and speed dating parties but found she had more fun at non-dating get-togethers, like adult summer camp and run club. It was at one of these social gatherings, hosted by a friend on the periphery of her friend circle, where Jackson met her now-boyfriend. Her only intention going into the event was simply to talk to people. Finding romance was a bonus.
“I feel very strongly that one of the reasons that we clicked so well is because, at least on my end, I was just hanging,” says Jackson, a dating and relationship coach who also hosts a popular dating advice podcast, Finding Mr. Height. “I wasn’t thinking about how I was coming across or trying to meet someone.”
In the last few years, many singles’ disillusionment with dating apps seems to have reached a breaking point. Some app users are tired of the lack of civility of online dating: According to a Pew Research Center Survey, over 85 percent of respondents ages 18 to 34 said someone on a dating app continued to contact them even after they said they weren’t interested. Others bemoan the jarring nature of going from strangers to romantic interests within days. A Forbes Health/OnePoll survey found 79 percent of Gen Z respondents were burned out by dating apps. On TikTok, videos with views in the hundreds of thousands urge viewers to delete their apps, while tearful young women recount their dating disasters, both on and off apps, wondering why it’s so hard to meet someone or make a genuine connection. The market value of Bumble and Match Group — which owns Tinder, Match.com, OkCupid, Hinge, and more — has plummeted by over $40 billion since 2021.
Although would-be lovers have, for nearly all of existence, found other ways to meet, some singles — especially ones whose only dating experience has been digitally mediated — may find their in-person flirting skills lacking. The key to connecting with someone in the flesh, experts say, is to focus on quality conversations with everyone you meet and not to take rejection personally.
Prioritize social events where you know you’ll meet new people
One of the biggest challenges to in-person dating is not knowing where to meet people. There’s the clichés — bars, parties — and locations ripped from rom-com plots — elevators, bookstores. But the key is to find a place where there are people you don’t know. Think of an activity you like to do and find a club or gathering around that pursuit, says relationship expert Susan Winter. Try not to think of these social events as opportunities to meet a potential romantic partner, but as chances to learn more about something you’re genuinely interested in, Winter says. If you’re having fun, it takes the pressure off.
The best tips for IRL flirting
Go to recurring social events — like a softball league — where you don’t know many people
Uncross your arms, take off your headphones, and make eye contact
Chat with three, four, or five strangers, regardless of whether you’re interested in them romantically
If the person you’re talking to is giving short, clipped answers and isn’t making eye contact, best to exit gracefully
If you’re into someone, ask them if they want to get together outside of the event
Don’t beat yourself up if they don’t reciprocate your feelings
These can be one-offs, like a concert, or a routine event, like an amateur softball league. However, the more frequently the group meets, the less intimidating it is to approach people, since they’re already familiar with you. “My biggest tip for people that feel more introverted or like they’re scared to walk up to people,” Jackson says, “is to do that more recurring event so you can establish bonds with people until they’re not strangers and it doesn’t feel so scary.”
If you’re up for attending these events alone, go for it — it’ll push you to chat with more people. To signal that you’re open to being approached, Ida Taghavi, licensed clinical psychologist at Williamsburg Therapy Group, suggests making eye contact with others, uncrossing your arms, and squaring your face and body toward people you want to talk to. Take off those headphones, too. (If you’re unsure whether someone is interested in being approached, look for these same signs in others.)
Winter says there’s nothing wrong with asking a friend to tag along, ideally someone who is also open to talking to new people. Small groups of two or three are great, Jackson says. The larger the crew, the less likely a stranger will approach you. “If you’re in a group of eight people, [it’s] highly unlikely that somebody is going to approach that group,” she says. “That’s just super intimidating.”
One of the few places where it’s not a good idea to meet a prospective partner: the workplace. Think twice about attempting to date a coworker. Sure, you may have a good read on their personality, but you risk making the office uncomfortable if the relationship doesn’t pan out. Plus, any power imbalance between you and your romantic interest may create an inappropriate relationship. If you do decide to pursue a colleague, review your company’s rules about dating coworkers and let things develop slowly at social gatherings outside of work, Jackson says.
Take romance out of the equation
Dating apps take the ambiguity out of meeting people: The fact that a person is on the platform and has matched with you is a pretty good indicator that they’re open to dating you. IRL interactions are far murkier. While people are rightfully concerned not to come across as creepy when approaching others, experts say the best course of action is simply to chat with someone not because they’re a “prospect,” but because they are a person worth talking to.
Don’t focus on flirting and instead flex your conversational skills. Try complimenting a stranger at the bus stop or asking if the person sitting next to you at the bar would recommend the book they’re reading. Listen carefully to their responses, Winter says, and ask follow-up questions based on what they’ve said. Soon you’ll find something you’re mutually interested in. “If you get boxed up, forget that they are a romantic prospect,” Winter says. “Actually tell yourself they are a human being and your task is to engage with this human being.”
It’s completely fine to be nervous approaching someone you don’t know, says Bela Gandhi, dating coach and host of the Smart Dating Academy podcast. But the best way to overcome those jitters is to talk to more people, she says. Start in low-stakes environments, like the grocery store, and try chatting with the least intimidating person you encounter. “Have a couple of icebreakers in your back pocket that you can talk to people about,” Gandhi says. “It’s about doing the reps. Doing the reps builds confidence.”
Another way to get your conversational reps in, Gandhi says, is involving your friends. For instance, while at a volunteering event, challenge yourself and a pal to have conversations with three new people over a 30-minute period. Then, you can touch base after.
“You might need to be the conversational leader — that’s not desperation, it’s socializing”
It’s important to pay attention to the other person’s verbal and nonverbal cues to determine whether they’re enjoying the conversation. If they’re giving you short, clipped answers and aren’t making eye contact, they might not be interested, Winter says. You might consider gracefully exiting the conversation to avoid wading into creepy territory.
Most of us would love for an attractive stranger to approach us at a party, but “everybody wants someone else to do the approach,” Gandhi says. You might need to be the conversational leader — that’s not desperation, it’s socializing. Even if you don’t connect with someone romantically, they have the potential to be a new friend, a professional connection, or even someone who can set you up with one of their single friends.
Asking someone out doesn’t need to be awkward
Maybe you’ve been chatting to someone for a while and the conversation is flowing: You’re laughing at each other’s jokes, there’s lots of eye contact, you’re both asking the other questions. All signs are pointing to mutual interest in getting to know each other better.
You don’t need to explicitly mention you’d like to go on a date with them, Jackson says, but keep it light by saying, “This was really fun. Maybe we could try that new [wine bar/restaurant/tennis court] you mentioned sometime,” or “We should totally exchange numbers and meet up at the [mutual favorite band] show next week.”
You could take another approach for crushes you see at recurring events. If the object of your affection is, say, another student in your pottery class, try asking the entire group if anyone wants to grab food afterward, Jackson suggests.
The ball is in their court now and you have to be open to any outcome, good or bad.
Be chill if you get rejected (and be chill when rejecting someone)
People might have a multitude of reasons for turning down a date. They could be in a relationship already, they might be moving to a new city in a few months, or they may just not feel the romantic spark. It’s okay to take it personally, Winter says. If they were brash and unkind in their response, you dodged a bullet.
Try not to get stuck feeling like you’re not worthy of love or attractive enough, Gandhi says. Instead, put yourself in their shoes, Jackson suggests. Imagine a time when a perfectly fine person asked you out but you weren’t feeling the spark. Chances are you weren’t thinking the person was unworthy of romance. “I wouldn’t feel embarrassed for a guy if he came up to me and struck up a conversation and asked for my number, and I was like, ‘I actually have a boyfriend. I’m not interested,’” Jackson says.
If they were brash and unkind in their response, you dodged a bullet
As obvious as it may seem, do not insult the other person if they decline a date. “Respect the other person’s decision and simply move on,” Taghavi says. “The relationship that is for you is one where both you and your partner feel aligned on your intentions.”
If you’re the one turning someone down, always be kind and direct. You might say, “I’m so flattered, but I’m seeing someone. I’m sorry,” or “I really enjoyed our conversation, but I’m not interested.”
There’s always the risk that the other person might not take your rejection kindly. That’s their problem, Jackson says. Now you know for certain you made the right call. “If somebody reacts to your very clear, kind communication with that attitude,” she says, “that sucks for them. That’s really unfortunate that they move through the world with that lens and I feel bad for them.”
Dating IRL can be an emotional minefield, but you can take the pressure off. So long as your expectations are to simply have a pleasant conversation with someone, the romance will soon follow.
