Anna Morgenstern of Dating Rehab NYC: How to Improve Your Dating Life and Choose Happiness

Posted January 7, 2019 by

The December 2018 issue of “The Atlantic” includes an article titled “Why Are Young People Having So Little Sex?” The story’s writer, Kate Julian, covers a lot of ground, including how technology has stifled our ability to interact with strangers in person. At one point, Julian recalls her conversation with a young woman about the foreign nature—the impossibility, even—of talking to a romantic interest in real life. The topic came up during a discussion of “Sex and the City” reruns:

“Miranda meets Steve at a bar,” she said, in a tone suggesting that the scenario might as well be out of a Jane Austen novel, for all the relevance it had to her life.

Dating has largely become a URL-centered world of confusion and stifled feelings. As a result, people are seeking out real-life connections, and Anna Morgenstern is here to help. As a dating coach and matchmaker based in New York City, Anna has spent several years teaching her clients how to “Make connections IRL again.”

I recently talked to Anna, and found some interesting similarities between her work and Inside8®.

Joe Jarvis
You lived in San Francisco before moving to New York. You’ve said that those two cities have really different dating cultures, and that those differences inspired you. What’s so different between San Francisco and New York?

Anna Morgenstern
In San Francisco, there were more men than women. Because women in San Francisco outnumbered men, the ladies had more dating options. Men had to be on their best behavior. But in New York, there are more women than men, so men control the dating culture. They want to be single and keep their options open. When I came to New York, I was just shocked. I had so many girlfriends who were beautiful and smart and successful, but they couldn’t figure out their personal relationships. It inspired me to bring a little hope back into dating, to tell people, “You don’t have to rely on dating apps. You can take control of your dating life.”

Joe
It seems like you anticipated that people would start moving away from the apps. What tipped you off?

Anna
It was really cool and exciting to use dating apps, but now I feel like people are sitting at home, swiping right in their little silos, and they’re kind of starved of real connection. There’s nothing better than being around people who make you feel good, and when you meet someone through friends, you can trust that person and you have some familiarity with them. Online, you don’t really know what you’re going to get. I think people want to meet someone the old-fashioned way. It’s sort of a lost art.

Joe
You’ve mentioned catfishing as a common danger when dating. Is it really that common for someone to look completely different in real life than they do online?

Anna
Oh, yeah, absolutely. A lot of people want to put their best foot forward. Apps like Facetune are very popular these days. You can make yourself a little bit skinnier or clear away acne. You want to project this version of yourself that’s quote-unquote “perfect.” On social media, we see all these Instagram models and celebrities who look so amazing, and dating online you’re seeing this extreme version of someone that isn’t their real, day-to-day self.

Joe
Also, if we’re comparing those false appearances to how we feel internally about ourselves, that can be dangerous, I would think.

Anna
We’re judging our real lives by other people’s fictitious lives. You don’t really know what’s actually going on behind the images of other people. We don’t post the bad stuff. We just post what we want people to think of ourselves. So it does cause people to actually feel depressed. We see all these people leading amazing lives. They’re traveling, looking amazing, and doing cool things. But we have no idea of what’s actually going on. I think people are realizing that it’s all fake. People want to get back to reality.

Joe
And  you help people get back to reality with coaching and matchmaking. How does all that work?

Anna
People come to me because they feel like there’s something they need help with. They might not be over a past relationship, or they’re really shy or need a little more confidence. They want to gain tools to help them feel confident and empowered. They don’t want to hide behind dating apps and stay at home not being social. My whole thing is meeting IRL, in real life. I believe the best way to meet someone is through a connection, a friend or someone who can vouch for the person. Also, people want to find tools to feel empowered and happy. If they see someone and they want to say hi, they can learn exactly how to do that and make it feel organic and natural and not to be scared of losing another opportunity.

Joe
So what you do is really a mix of things, depending on what the person needs?

Anna
I customize the program for each person. I develop different homework assignments and we start with baby steps. Then the homework assignments get more advanced as the client feels more comfortable starting conversations with strangers. One simple thing is I tell them to praise themselves every day. We have an innate ability to see everything we do wrong. We don’t really ever step back and see all the things we do right.

Joe
All of these skills sound applicable to life outside of finding love as well, whether it’s your job or family or whatever.

Anna
Well, if you’re nervous about having conversations with people, that’s going to affect your work life. Being comfortable speaking to people comes from being confident about yourself, being internally happy. And that comes from filling your life with activities and events and things that make you feel fulfilled. Across the board, when you’re coming from a positive happy place, people are going to want to work with you. You might get a promotion because you’re letting yourself stand out a little bit more, not being nervous or shying away from presentations or taking on new projects. It absolutely applies to every aspect of your life.

Joe
Talking to you, it feels like there’s a similarity between what you do and what Inside8® does. Like, you can step back from unhelpful habits, unhelpful ways of thinking, and see new possibilities in your life again.

Anna
After taking the Inside8® test myself, it tells you when you’re at your best versus when you’re at your worst. At my best, I’m being creative and working with others and sharing ideas with others. At my worst, I keep it to myself and ignore people and I kind of work in my own little silo. Since I took the test, I notice when I’m not collaborating with other matchmakers, or even sharing my ideas with friends or family. I’m not as happy and positive and feeling optimistic. I’m able to see that and snap out of it, like, “Well, I’m at my worst right now, and I don’t want to go down that path.”

Joe
Which Inside8® group are you in?

Anna
I’m a Holistic.

Joe
Oh, that makes total sense. Holistics tend to be comfortable on their own but they need to be social to really thrive, so I see what you’re saying about realizing you’re in a silo and making a change.

Anna
Yeah, that has been really powerful to me. I can choose to break out of that. When things happen, you can choose how you react. You can choose your mindset. When you put good energy out there, it comes back to you 1,000 percent.

Want to find out how to overcome negative feelings and get back to your best, whether it’s in romance, at work, or with your family? Take the Inside8 personality test and get your own report.

Joe Jarvis

Joe Jarvis is co-founder and editor of Someone Else, a style journal and production agency based in Chicago. Joe focuses on the core motivations of clothing designers and artists, to help tell their stories. With The Jarvis Report, Joe uses the same approach to discuss personal fulfillment with people in the world of Inside8.

All stories by: Joe Jarvis

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