ASK THE DATING COACH: A romance expert answers your questions on dating as a highly sensitive man, how to navigate texting mishaps, and canceled dates.
Dating As A Highly Sensitive Man
After two pretty good dates with a woman, I invited her to my place for date no. 3 to watch “Titanic.” She had never seen it. I got emotional and teared up during the scene where an old couple are in bed holding each other as the ship goes down. I was planning to go for a first kiss after the movie, but as soon as the credits rolled, she said, “Well, it’s getting late!” and left. I haven’t heard from her since. I feel rejected! I thought women wanted emotionally open men. Did I show too much vulnerability?
—Ryan, 33, Austin, Texas
No judgment here, Ryan. I cried while watching “A League of Their Own.” (And I wanted to cry during “Fast Five,” but that’s because of Vin Diesel’s “acting.”)
That “Titanic” scene is heartbreaking, not to mention watching Leonardo DiCaprio’s Jack Dawson meet his icy end. (Come on, Rose—there was plenty of room on that door!)
Ryan, you’re worried that showing emotion and vulnerability is an iceberg that will sink the S.S. Romance. But vulnerability on a date isn’t weakness. It’s strength—as long as you pair it in the right measure with fun, flirty, authentic confidence.
On my first date with my girlfriend Jessamin, I told her about my failed nine-week marriage, and how clueless and insecure I used to be before I became a dating coach—not exactly “Bachelor” highlight-reel footage. But I balanced my openness with playfulness and masculine presence.
Our date had spark, humor and variety—much like Jack and Rose had moments of fun (dancing below deck) and vulnerability (Jack admitting that he’s a drifter with no money or a permanent home).
My questions for you as a highly sensitive man: Did you flirt with her? And did you lead the dates with energy and confidence? Since you hadn’t kissed her by date three, I suspect the romantic momentum may have already been cooling for her, tears or not. Women like men who lead the dating dance.
Rose falls for Jack not just because he’s a free-spirited artist. She’s drawn to his passion. He stands up to her arrogant fiancé, makes her laugh, and sees her as a person, not a prize. Jack isn’t just emotionally open. He shows leadership, playfulness (see: spitting contest), kindness and strength.
If she lost interest in you, it wasn’t because you’re sensitive enough to cry. It was because she didn’t feel you led the dating dance.
She can cry with her best friends. On a date, women tend to want connection and chemistry with a man who leads.
So when courting a woman, let your vulnerability be one brushstroke in a captivating, colorful romantic canvas. Being a highly sensitive man is part of who you are, and so you shouldn’t hide that.
The right woman will tear up with you and share the couch—unlike a certain young woman on a floating door.
Typo Negative
I was texting a woman I had just connected with on Hinge, and my phone auto-corrected and turned “Hey beautiful” into “Hey Boobzilla.” I was horrified! I sent her five apology texts! Now she’s ghosted me. It’s just so awkward. Should I move on?
—Dev, 48, Jersey City, N.J.
Oddly enough, “Hey Boobzilla” was also the name of my ska band in college.
Dev, the typo’s not what got you ghosted. It was likely your five-text apology tour that followed.
I’ve been doing improv comedy for many years, and there’s a saying: “There are no mistakes—only gifts.” If an improv actor says something weird or “wrong” on stage, their scene partner doesn’t correct it. They use it. If I meant to say birthday cake but I accidentally said birthday kale, guess what—my character is now blowing out candles on a salad. That’s unusual, which is what makes it funny.
You can see texting mistakes the same way. Don’t hit the panic button. You could have said something like, “Whoops, I meant to say, ‘Hey beautiful,’ but my iPhone has named you Boobzilla. I guess that makes me… Sir Faceplant? Or would you like to pick my nickname?”
See how light and playful that is? That kind of response clears the air and shows that you’re confident enough to laugh at yourself.
Your typo wasn’t awkward. Your over-apology was.
See your next texting mishap as a gift, not a gaffe.
Cancel Culture
Last week, I had two women cancel dates with me. This is a frustrating pattern! I’ll set up the date, and she seems into it. I’ll go quiet for a few days so that I don’t seem needy. And then the day before the date, I’ll text her to see if we’re still on—but she backs out. Can you help?
—Marcus, 36, Denver, CO
Dating plans are like songs on a Spotify playlist—easy to make, easy to skip.
I have two simple “don’ts” for you.
First, don’t go radio silent after you set up the date, or else she may lose interest. Most women prefer some communication with a guy leading up to meeting. There’s nothing needy about a light text every other day or so to keep both of you excited about the date. (“Just three more days until you get to experience my karaoke voice, which only dogs can hear…”)
Texts sent in the days leading up to a date are like movie trailers that get her excited for the feature presentation—meeting you!
Second, don’t confirm the date like it’s a dentist appointment. Asking women “Are we still on for tomorrow night?” sounds like you’re bracing for a “no” while giving her an easy out if she’s on the fence.
Instead, keep the momentum going with an enticing text asking her a question that assumes all systems are go. Try something like, “Oh, just a heads-up… the Spanish place we’re going to tomorrow has AMAZING sangria. Are you Team Red or Team White?” When she replies she’s into white sangria (sacrilege!), then your date is confirmed.
My client Barry had to learn this lesson the hard way. He set up a Bumble date, went quiet for almost a week, and then tried to confirm things a day before the date. She texted him, “I’ll be honest…you went quiet on me and I lost interest. Just not feeling it now…”
If she does cancel, drop her a classy, funny line, like: “OK, but what am I supposed to tell my parents? They were so excited to meet you!” Your graceful humor may give her second thoughts and spark her interest again.
Dog-Gone It!
I meet a lot of dog lovers on the apps, but I think women like my corgi, Stan, more than they like me. They go crazy for him, but I never hear from them again. Thoughts?
—Jared, 34, Minneapolis
Well, at least someone in your home is enjoying some heavy petting.
Connell Barrett is a dating coach for men. He’s helped men all over the world find the woman of their dreams. Connell has appeared on The Today Show, Access Hollywood, and in publications such as NBC News. Book a free call with Connell below.
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