Dating coach Connell Barrett answers your questions on how to escape the friend zone on first dates, becoming more charismatic, and dating tips for a post-pandemic world.

Escape The Friend Zone

Do I have to go for the kiss on first date? I feel stuck. On one hand, I know I need to make a move or else I’ll have to escape the friend zone. On the other, I don’t want to make a woman feel uncomfortable with a forced kiss. What do I do?

—Eric, 27, Oklahoma City

Here’s a quick story, Eric, about what NOT to do when you want to escape the friend zone. It happened to me over a decade ago, when I was going on tons of dates to try to “crack the code” of connecting with women.

Stephanie and I were walking to the subway station after a first date.

“Kiss her,” I thought as we walked to the subway station. “It’s now or never.”

When Stephanie and I stopped at a crosswalk near the end of our first date, I went for it. But she had been checking her phone, so when she looked up, my incoming lips must have seemed like a sneak attack. She recoiled, and I caught the corner of her pursed mouth.

“God, I’m so sorry,” I said, feeling clumsy and creepy.

“Umm, it’s okay,” she said, vanishing down the steps to catch her train. “G’nite.”

There was no second date.

Looking back years later, I now realize my rookie mistake. I call it the Lunge.

It happens near the end of a date. Sensing that he’s been playing it too safe, a guy feels the pressure to make a move to keep from getting friend-zoned. But he doesn’t want his date to feel uncomfortable, especially in the #MeToo era.

Finally, feeling the need to do SOMETHING, he goes for the kiss, like a quarterback heaving a desperation, fourth-down pass. Surprised, the woman either pulls back or endures an awkward lip-lock.

So you definitely don’t want to sit on your hands for a three-hour date, and then lunge at her. She won’t appreciate the courage. It will seem try-hard and uncomfortable, for both of you. And she’ll probably not want to see you again.

Instead, take the “stair-step” approach. Take small, flirtatious steps—ALWAYS noticing how she’s responding so that you can adjust accordingly. (Empathy is just plain sexy.)

If you’re on a date, greet her with a warm hug. Move on to playful taps on her arm or shoulder. Hold eye contact. Open up and connect emotionally. Notice if she’s laughing, enjoying you, and initiating touch herself. Hold her hand. Is she holding yours back and leaning in? If yes, she’s ready to kiss. Go. Now.

Save your lunges for the gym.

Yawn Maintenance

Maybe I’m just a boring guy, but women on my dates yawn a lot. Any suggestions on how I can keep their interest and just be more interesting and charismatic?

—Dominick, 29, Los Angeles

Your dates are yawning? Easy fix. Instead of cocktails, take her out for a couple glasses of 5-Hour Energy.

Better yet, here’s a shortcut to charisma: Get good at storytelling. You want her dropping her jaw in awe, not in boredom.

We’re ALL hardwired to love stories. A good, personal story from your life makes you more charismatic, holds her interest, and invites her to share her own stories—which can amplify connection. Here are three storytelling tips.

1: Use a three-part structure: setting, conflict, resolution

Here’s a story from my teenage years that I’ve told on many dates: “I was in study hall in high school [setting] before a geometry test. I wasn’t ready, and if I failed I’d end up in summer school [conflict]. So I shut my textbook, went to the nurse, and pretended to have back spasms. When my parents came, instead of taking me home, they drove me to the hospital for an MRI and X-rays. I had to wear a hospital gown and everything. And the doctor diagnosed me with scoliosis—for fake back spasms! [resolution]. My poor mom started to cry, not realizing the whole thing was a scam.”

2: Details!

Specifics bring a story to life, making it more vivid. Your high-school English teacher was right when she scribbled on your term paper: “Show, don’t tell!”

In my story above, it’s the specifics (the textbook, the hospital gown, my mom’s tears) that makes it so vivid—and keeps the audience’s rapt attention.

3: Tell vulnerable tales

Avoid stories meant to make you look “cool.” It’s much cooler to laugh about an embarrassing moment from your past. For example, the time you struck out and lost the game, not the time you hit the home run to win the game. Vulnerability is powerful and attractive. My “fake scoliosis” story works in part because it makes me look like a schmuck. The story impresses not by trying to make me seem cool, but by my willingness to look like an idiot—and laugh about it.   

But don’t overthink it. Some of the best stories are just weird, funny incidents. Travel adventures work well. My client Craig loves telling his dates about the time his friends snuck him into Canada by rolling him inside of a carpet and putting him in the back of an SUV.

Getting Back in the Game

I haven’t dated in over a year because of the pandemic. For that matter, I’ve barely looked a person in the eye IRL. I’m probably gonna have to learn how to be with people all over again. Any help?

—James, 37, Fort Wayne, Indiana

If you feel anxious about “getting back out there” for IRL dating, remember—everyone will be nervous! In addition to dating butterflies, we’ll also have post-pandemic nerves. Remembering that we’re all in this together should relax you.

Here are some pointers to help smooth your journey from pandemic dating to a more normal world (bring it on!).

• Feeling the nerves? Be vulnerable and let your date know. You might text them the day of your date, tossing in a joke to break the tension. Something like, “I’m excited (and a bit nervous) to meet up—with an actual human! I feel like I just broke up with Zoom, lol.” Vulnerability is attractive, and mentioning that you have butterflies can paradoxically reduce them, helping you feel more confident and excited.

• Confidence comes in part from letting go of what you can’t control, such as a woman being into you. Turn your date into a guaranteed win. Remind yourself that it’s a huge success just to be on a real-life date after this seemingly endless pandemic. Once the date starts, you’ve succeeded—no matter how it goes. Sure, it would be great to make a romantic connection, but lower the bar for first-date success. You’ve just hit “reset” on your love life and begun getting back to normal. That’s worth celebrating.

• Give yourself one or two “back-pocket” topics—things you can ask her about just in case you get stuck in your head. If you know she loves skiing or took an exotic trip, be ready to ask her about it. Having a go-to topic or two gives you a conversational safety net, relaxing you. And because you feel more confident, you may not even need to use them.

• It’s fine to mention the pandemic, but don’t dwell too long on non-fun topics. It’s a date. You’re there to connect, flirt, have fun, and put your best, real self out there. A great way to discuss the pandemic is to share a cool project you pursued in your downtime. Maybe on lockdown you learned to bake, took up Spanish, or read “War & Peace." Brag a bit—and ask her how she spent her time. This lets you talk about passions, not the pandemic itself.

• You may be rusty when it comes to using your voice, body language and eye contact. Get to the date venue 10 minutes early and make small talk with the staff or other patrons—this will help you get your vocal tonality synched up with your environment, whether you’re at a quiet coffee-shop or a loud club. This is important because a confident vocal tonality sends attractive messages and vibes. Notice her eye color; this assures that you make good eye contact, another appealing social cue. And since you’ve been curled up on your couch for a year, check your body language a couple times during the date. Think, “Shoulders back, spine straight, chin up.” This not only looks confident and energetic, but it feels good, too. The way you use and hold your body affects your emotions and confidence.

Want some tips on dating tips for shy guys or flirty questions to ask a girl? Read Connell's column here and subscribe so you never miss an update!

Want to be coached by Connell? Order the book Dating Sucks But You Don't, and learn how to approach women and get the girl here. It comes with incredible bonuses like live group coaching!

Connell Barrett is a NYC dating coach for men. He's helped men all over the world find the woman of their dreams with actionable advice such as what to say on Tinder and how to get a girlfriend. His work has been featured on Access Hollywood and the Today Show. In addition, you can find him in print in Maxim, O Magazine, and Cosmopolitan. Ask Connell a question below!

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