I went to a flirting class with a dating expert and she taught me her 4 surefire techniques to attract dates

·7 min read
Two women sit back-to-back, smiling and texting on their phones.
Crystal Cox/Insider
  • I took a one-on-one flirting class with a dating expert who specializes in text-based flirting.

  • She said leading with curiosity is more important than finding a match who is similar to you.

  • We practiced flirting via text message, during a first date, and with a random stranger.

  • Visit Insider's homepage for more stories.

On any given day, you can find Amy Nobile sitting in front of eight iPads, messaging singles through different dating profiles that belong to her clients.

As the founder of Love, Amy, Nobile works one-on-one with singles to teach them how to flirt on dating apps, secure quality matches, and find meaningful relationships.

Through the iPads, Nobile is able to log into her clients' dating app profiles at the same time they do. It leads to a collaborative experience, where Nobile show clients how to flirt over text and then lets them take the wheel.

For $10,000, clients get four months of flirting coaching, in-person date coaching, and on-demand support from Nobile.

I met with Nobile in her West Village apartment in Manhattan, where she walked me through the lessons she teaches singles looking for love.

This is Amy Nobile. She the founder of Love, Amy, a dating app-focused matchmaking service.

A woman with blonde hair sits on a couch and smiles.
Crystal Cox/Insider

Nobile started Love, Amy in April 2019 after she reinvented her career and love life following the end of her 20-year marriage.

She immersed herself in dating apps out of sheer curiosity.

"I'd heard of some of the apps, but the only resource I had were a few single girlfriends who had nothing but negative things to say about them," Nobile, a former publicist, previously told Insider.

Now 52 with a boyfriend and new matchmaking career, Nobile told Insider she's "happy beyond" her dreams and is passionate about helping others find the same.

She started her business playing cupid for friends, but word spread and now Nobile works with a roster of paying millennials and over-40 clients.

Nobile runs her dating app service out of her apartment in Manhattan. That's where I met her for our one-on-one session.

One woman walks towards another woman sitting in a chair in a living room.
Crystal Cox/Insider

The moment I walked through Nobile's door, I could feel her warmth and understand why singles put their dating lives into her hands.

Before meeting a client for a full session, Nobile interviews them about who they are and their relationship history.

Two women sit at the end of a table and face each other while talking.
Crystal Cox/Insider

Nobile said she gives every new client a 10-page intake form, where they answer questions about past romantic relationships, their history with psychotherapy, their interests, and what they're looking for in a partner.

This information will help her work with a client to figure out which dating-app matches to pursue, and which to let go of.

Next, Nobile explained what fruitful flirting entails. To my surprise, she said it's more about your attitude than what you're talking about.

A woman in a black top sits at a table talking to a woman in a green dress who faces away from the camera.
Crystal Cox/Insider

When Nobile asked what flirting means to me, I said, "I just think of playfulness, and not taking things too seriously. It's another way to feel intimacy, but less serious."

Nobile generally agreed with my definition, and also said good flirting is characterized by "warmth."

"Connecting on a deep level is the new flirting — energy, vibing, all that stuff. Flirting is about connecting on an energetic level, in my mind," Nobile said.

She said the idea that flirting means being inauthentic, or putting on a show for etiquette's sake, is antiquated.

Instead of searching for a date who shares all of your interests or perspectives, Nobile suggested getting curious when differences do arise and find a love interest who does the same.

To practice flirting over dating apps, Nobile printed out a real man's Bumble profile and handed it to me. She instructed me to play myself and send an initial message, and said she'd play Mike, my mysterious suitor.

A close-up of a paper printed with a man's dating profile.
Crystal Cox/Insider

When I saw Mike's profile, it said he didn't understand the concept of a nap. I froze. How could I flirt with someone who explicitly dissed one of my favorite pasttimes?

Still, I tried my best to keep things light by writing, "Mike! We need to have a talk about your disdain for naps."

Nobile didn't take it easy on me. As Mike, Nobile played up our differences and questioned our compatibility. She wrote that my love of napping could be a deal breaker.

Women sit back-to-back in chairs, looking at their cell phones as part of a flirting exercise.
Crystal Cox/Insider

I texted Nobile-as-Mike, saying she must've never had a life-changing nap before.

But when she responded, saying that difference could mean our match was off the table, I was stumped.

Unsure what to say next, I decided to end the text banter with Nobile-as-Mike. I wrote, "Fair enough."

A woman uses both thumbs to text on her phone.
Crystal Cox/Insider

Nobile told me not to worry, as flirting via text is the concept her clients find hardest to grasp.

Two women sit back-to-back, smiling and texting on their phones.
Crystal Cox/Insider

That's why Nobile often invites clients to sit side-by-side and banter with dating-app matches together.

She uses what she's learned about her clients' personalities, interests, and desires to suggest how a flirtatious conversation could go, with the ultimate goal of setting clients free to flirt on their own.

After admitting my worry of coming off too negative during the dating app test, Nobile also showed me a Tyra Banks-inspired exercise she does to get into the flirting mindset.

A woman in a black top walks towards the camera, looking out towards another woman walking away from the camera.
Nobile said she "flirts with her eyes" to complete strangers and it instantly boosts her mood. Crystal Cox/Insider

Nobile turned "smize," Tyra Banks' made-up word for "smiling with your eyes," into "flies," or "flirting with your eyes."

She said the exercise gets people in the mood for online dating because they're already in touch with their warm and curious sides before matching with a stranger.

To smize, hold eye contact for three seconds with someone walking by in the opposite direction, said Nobile. As you're about to pass each other, offer a smirk or brief smile, depending on your audience.

"If it's a hot person, you might have a slightly different look in your eye than with an 80-year old-woman," Nobile said.

For my final test, I had to flirt with Nobile during a mock first in-person date.

Two women sit at the end of a table and face each other while talking.
Crystal Cox/Insider

I haven't been on a first date since my senior year of high school, so I was nervous I would blow my fake date.

According to Nobile, a first in-person date should happen after you've spoken on the phone for a few minutes at least. When you meet, keep it to 30 minutes and grab coffee or an early drink so you can reflect on the experience after, said Nobile.

For our date, I started with asking Nobile how her day went, to which she replied, "I don't love my boss right now, so it's a little tough. I mean, sorry, just kind of a stressful day."

I could tell the real Nobile was testing my ability to handle negativity, so I responded with, "I can totally relate to that, but I'm glad we're here now."

Eventually, the conversation turned towards riding bikes. Since I previously interned at Bicycling magazine, I mentioned that commonality and asked how Nobile got into the sport in the first place.

The conversation flowed from there. After, Nobile complimented my warmth and ability to make the conversation feel personal. She added that maintaining eye contact and flashing a smile every once in awhile can add extra warmth to the first date.

Once Nobile gets clients through the flirting phase, she supports them as they get to know a match through real-world and on-demand dating advice.

A woman sits on a wide window sill and looks out a large window.
Crystal Cox/Insider

Once Nobile's clients secure matches they like through their flirting sessions, she offers advice on how to discuss values with dates and determine if they could be a long-term connection.

She pushes them to go on two to three video or phone "screener" dates every week, and has weekly phone check-ins with clients to keep them accountable.

Her dedication doesn't stop there. On weekends and during late nights, Nobile makes herself available on-demand.

"I believe this is such an intimate thing. I've had clients call me from the bathroom during a date or before a date on a Saturday night," said Nobile.

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