The Scoop: Dating coach and matchmaker Anna Morgenstern encourages women to venture out of their comfort zones and into “the wild” — the real world, where dating is more complicated than zippy bios and filtered profile pictures. She provides tips and tricks to help women gain confidence in the real-life dating scene.

There was a time when lifelong connections formed “in the wild.” A dive bar was the proverbial watering hole, and tipsy singles flirted like lions in heat. Nowadays, iPhones instead of candles illuminate tables, and it’s the ding of the notification bell — not the hum of romantic conversations — that echoes through restaurants. 

Technology, societal changes, and the pandemic have made it harder than ever before to make authentic connections. Many of us have retreated into the relative safety of dating apps.

That’s why dating coach and matchmaker Anna Morgenstern has made it her mission to teach singles how to make lifelong connections in the outside world — no swiping or pinging necessary. 

Screenshot of logo from Anna Morgenstern's website
Anna Morgenstern helps singles from all across the country find true love in the real world.

“I wanted to create my own matchmaking business where I also do coaching, as well as helping people meet in real life. To tell them where to go, and how to approach people,” she told us. Her coaching philosophy is simple: to remind women of their own innate power in the real-life dating world. 

“I’ve just felt so passionate about creating a space where women felt empowered, because we do date in a patriarchy,” she told us. “It feels, as a woman, that we don’t have a lot of control.” 

Women may have much more power in the offline dating world than it seems. As Anna explained to us, finding romantic success without the help of dating apps can start, ironically, with the help of technology. You just have to know how to use it to your advantage. 

Use Technology as a Tool in Real Life 

Apprehension about matching with a potentially dangerous person, or even just a catfish, has made some people more hesitant about online dating. “I got scammed by a guy I met on a dating app once,” Anna admitted. “It’s happened to a lot of women that I know.” 

This doesn’t mean people are gung-ho about dating offline, however. “Both sexes really do feel like there is a disconnect in dating. It doesn’t really feel safe, or like something they’re excited about,” Anna said. 

If meeting people IRL makes you uncomfortable, of course you’re going to retreat to the more contained digital world. A problem arises when people depend solely on dating apps to make romantic connections. 

“We don’t have to depend on [dating apps],” Anna reminded us. “There’s no point in doing something again and again that’s making you depressed or anxious or feeling rejected,” she said. The same goes for dating offline as well. If the apps aren’t the way to go, but the real world is still too intimidating, then Anna suggests a happy medium. 

Woman holding phone hand over mouth
Use Google, Facebook, and Instagram to connect with people who share your interests. Then meet in real life.

Use technology as a tool, not a guide, for dating in real life. The barrier of a screen prevents you from making real connections in the outside world, but the apps can still function as a jumping-off point. She named Facebook and Instagram as two useful tools. “Now that we have the internet to search … you’ll find a community in whatever you’re interested in,” Anna said. 

“If you have an interest in something, [the internet] is an amazing place to meet like-minded people.” The opportunities are there, Anna says; you just have to be open-minded enough to look for them. “We’re seeing a huge push in events and meetup type groups, athletic communities, book clubs, whatever it could be.” 

Dating apps give women the option to block unwanted advances, something they can’t do as easily in real life. But Anna has urged her clients to embrace the unpredictability of the outside world, while using modern technology to make dating a safer, more fun experience. 

“All this technology has made us become loners and live in our houses and not depend on community,” she said. But by using social media to research local organizations, groups, and clubs that share your interests, you’re increasing your chances of making friends, allies, and a potential love connection. 

Technology helps you to connect with like-minded individuals. Once you’ve found your niche, it’s time to put the phone down and start socializing in the real world. 

Authentic Connections Start With a Single Question 

Socializing without your favorite Distraction Rectangle (AKA, your cell phone) can be intimidating, especially when you’re trying to meet people in real life. Many of us haven’t flexed our social muscles in quite a while. It feels like we weren’t born with “socializing genes” at all. 

But Anna insisted that this isn’t true. “You actually have all the control as a woman because you have what every man wants. Men have fought wars for us, changed religions of countries, and I think a lot of women kind of forget their power in dating.” 

Anna had some socializing tips to make socializing much less agonizing. One strategy she suggested is to play a more modern variation of the damsel in distress. But instead of playing dumb, ask insightful questions that connect to a shared hobby or interest. “Men love to play saviors, so play into that,” Anna suggested. 

Anna used a gym encounter as an example. If you see someone you’re interested in at the gym, and they’re using a machine you’ve never used before, ask them for pointers. “Ask what they’re doing and try to start a conversation,” Anna said. 

Not every conversation needs to end in a marriage proposal. Go into conversations with the intent to make a friend, not necessarily a romantic connection. This takes some of the pressure off and can make the man feel more in control without you giving up any of your own control. 

Friends laughing and drinking at table
Happy Hour is a great opportunity to break out of your comfort zone. It encourages natural socialization but doesn’t lock you into an all-night commitment.

“I do have a favorite secret weapon: I love a happy hour situation,” Anna told us. “Tell your friend to meet you there at 6:00 p.m. Get there at 5:45.” Find a group of people you’re comfortable approaching and ask if they’ll keep you company until your friend arrives. “If [no one in the group] is a fit for you, in 15 minutes, your friend will be there. No harm, no foul.” 

The gym and happy hour scenarios give women the opportunity to approach first — to stay in control — and the opportunity to slip away if need be, all while boosting the man’s confidence. He can feel good about helping you, and you can feel good knowing that you made a positive impression on a potential partner. 

When it comes to approaching people in public, Anna recommended that you keep the conversation honest and straightforward. “Be authentic, because if it feels forced or inauthentic, the person’s gonna get weird vibes … just make it natural, and if they’re interested, you’ll feel the energy.” 

Rejection Hurts, But it Doesn’t Have to Scar 

An obvious downside to “putting yourself out there” in the real world is the possibility of rejection. But if you let the fear of rejection run your dating life, you’re not going to get very far… and you may inadvertently block viable connections. 

“You match the energy you put out,” Anna said. “What you think then translates to what you say and then translates to what actually happened.” If you think negatively about your dating prospects, or live in fear of rejection, it’s going to show in the way you interact with people. “That’s what you’re manifesting, that’s the energy you’re putting out.” And, Anna warned, “You’re actually going to attract more of those kinds of people.” 

That’s why Anna has encouraged her clients to focus on the positives. “A lot of people are so scared of that rejection, but that person will never think of it again,” she pointed out. Think about it: Do you dwell on the person you politely turned down at the club? Probably not. 

Screenshot of Anna Morgenstern from her website
Anna Morgenstern encourages her clients to take rejection in stride.

In fact, you should congratulate yourself for trying at all. “You tried something, it didn’t work. That’s amazing. It’s a huge win,” Anna said. “Most people don’t ever have the balls to go up to someone, and so congratulate yourself on doing something that’s hard.”

Anna suggests women relax a little about dating and rejection, and avoid overcorrecting to the point of indifference. “If you’re saying you don’t care and you don’t want it, then you’re not going to get it,” Anna warned. As with most things in life, dating is a mental and emotional balancing act. 

There are so many more unknowns when you take your dating skills off the apps and into the real world. But as Anna said, having a positive mindset is one of the “easiest things that you can change if you can’t change anything else.” 

Only when you’re offline can you sense someone’s authentic energy, and compare it to your own. “A really good thing to do is think about how you can connect to others and how you can help others, and that energy will come back to you,” Anna said.