Connell, men say I’m “intimidating” on dates, and then they ghost me. It’s happened three straight times. What’s wrong with me? Why are men intimidated by me?
THE ACCIDENTAL ICE QUEEN
Nothing. You’re golden—but guarded.
When confident men call you “intimidating,” what they really mean is, “I couldn’t tell if you liked me.”
Chances are, you don’t want to seem too eager on dates, so you hold back. You hesitate to flirt, either because you don’t know how, or you’re afraid of being vulnerable.
To you that feels safe. To him it feels like the Berlin Wall.
The typical man fears rejection. If he doesn’t get clear signals that you like him, he’ll say, “She’s cold—just not into me.”
What feels like poise to you feels like indifference to him.
You think you’re projecting Grace Kelly, but you’re closer to Mona Lisa.
My former client Pamela did this, too. She’s a physician and a successful businesswoman, but that’s not why men felt intimidated.
She shut down on dates and let her shyness—her fear of flirting and coming off as try-hard—keep her real, warm self from coming out.
The fix, I told her? Send him clear signals. Give green lights.
This scared Pamela. She worried, “I don’t want to seem slutty.” But she was tired of getting ghosted by men.
On her first date with Richard, she told him, “You’re very handsome—and I didn’t expect to find you this charming this quickly.” He lit up like the Hollywood sign and asked her out for a second date before the first date ended.
They kept seeing each other, and they’re now engaged.
As Pamela learned, there’s nothing wrong with you. You’re just not giving men what they love: a clear, direct compliment.
So here’s your 4-step “Green Light Playbook” for your next first date.
1: Give one sincere compliment: “You’re charming and fun to talk to” makes a man feel like a king.
2: Tell him you’re having fun—out loud. (He’s wondering.)
3: Laugh out loud, freely. It puts guys at ease.
4: Before you part ways, give him the gift of clarity with six simple words: “I’d like to see you again.”
You’re not intimidating. You’re just hard to read—but so are some of the best novels.
Open up and let him turn the page.
VIRGIN TERRITORY
I’m 33, and I’ve never had sex. It’s embarrassing being a male virgin. I feel this huge shame and pressure to hide it on dates. I’m scared that if I tell a woman, she’ll think there’s something wrong with me. How do I bring up this awkward topic without feeling ashamed or making it weird?
INEXPERIENCED IN ALBANY
We all have emotional baggage. Yours just feels oversized, when it’s really more like carry-on. (Which Spirit Airlines would charge you for, the cheap bastards.)
You have nothing to be ashamed of. Your worth isn’t tied to your sexual experience. The right woman will see that.
Your question touches on one of several taboo topics that men are terrified to talk about on dates, including bringing up your ex or discussing sexual history. But you should tackle these topics, as long as you do it the right way.
When you avoid scary subjects, you play it safe—and that can make you seem too safe to a given woman.
But when you face taboo topics head-on, you show the kind of edge and emotional courage that separates you from the dull dudes she’s been meeting.
Let’s start with your situation, and then I’ll walk you through some other taboo topics.
Taboo Topic #1: Sexual Inexperience/Being a Virgin
You may feel like you’re carrying a shameful secret. You might worry that she’ll think you’re weird or broken. But sexual inexperience isn’t a dealbreaker—it’s part of your story. What matters is how you talk about it.
One of my clients, Russell, was 35 and still a virgin when he hired me to be his dating coach. He was terrified to tell women that his bedpost had no notches, but on his first date with Brandy, he decided to own it.
He said, “I want to be honest with you—I’ve never had sex before.” He expected Brandy to pull away, but instead she appreciated his honesty.
A few dates later, they’re at his place, and things are getting hot and heavy on the couch. She says, “I want to be your first—and your last,” then takes him by the hand and leads him into the bedroom.
At long last, Russell lost his virginity because he stopped hiding and chose to own his sexual history.
If sexual inexperience is part of your story, don’t run from it. When the moment feels right on the first or second date, say something like, “I haven’t had much experience, and I’m okay with that. I just haven’t found the right person yet.”
For the right woman, that kind of honesty builds trust.
Your virginity does not define you. It’s a fact about you. No more, no less.
It’s not a red flag—just a post-it note on the fridge.
Taboo Topic #2: Talking About Your Ex
Most men avoid discussing their exes on first dates because they fear they’ll look bitter. What most guys miss is that talking about your ex the right way—by taking full responsibility for your role in the breakup—actually makes you more attractive.
When you own your mistakes without blaming your ex, you signal to your date that you have emotional maturity, self-awareness, and that you’re growing. You’re not a bitter ex-boyfriend pointing fingers. You’re a man who’s learned from experience.
On first dates, I’d often talk about my failed nine-week marriage. That’s right—I was once married for nine weeks. (It was over so fast, we fought for custody of the wedding cake.)
I never blamed my ex. I owned it. I’d say to my date, “Look, it takes two to tango, but I was the one tripping over my feet. It was mostly my fault. I settled because I was insecure, and I’ll never make that mistake again.”
Telling the truth is attractive. Women want men who have the confidence to own their mistakes.
On a first date, spend five or so minutes talking about your most important past relationship—but only through the lens of what you did wrong and/or what you learned.
On my first date with my girlfriend Jess, I said, “My failed marriage taught me to never make a commitment out of the fear of being alone—that’s not fair to her or to me.”
That one sentence told her I value growth and take relationships seriously—without being heavy or negative.
Taboo Topic #3: Talking About Sex
You likely avoid the topic of sex on dates because you’re afraid you may come off as creepy, inappropriate, or awkward. So you pretend it doesn’t exist.
But sex is woven into the fabric of dating and love. Avoiding the topic of sex on a date is like avoiding the topic of food at a restaurant—it’s already on the menu. It’s almost weird not to talk about it. And pretending sex doesn’t exist keeps dates safer and can land you in the friend zone.
The better approach is to introduce sex in an innocent, G-rated way and then see how she feels.
Here’s the best way to do it: bring up the topic of first kisses and crushes from your youth. Coming-of-age topics like first kisses and first crushes are innocent and 100% not creepy.
My client William brought up first kisses, and his date lit up. She told him that when she was 15, she kissed her boyfriend, their braces locked together, and their faces were stuck for five minutes. Adorable.
If she responds well, that’s when things can naturally drift into more PG-rated territory.
That’s exactly what happened with my client Aaron on a first date with Samantha. First, they talked about each other’s first kisses. Then they joked about what makes for a really good kiss. And before he even realized what was happening, Samantha raised an eyebrow and asked, “So, in bed, do you like a woman on top or on the bottom?”
That escalation happened because Aaron didn’t force anything. He started light, paid attention to how she responded, and followed her lead.
TRY HARD WITH A VENGEANCE
After a first date, I sent a woman a love poem and a dozen roses. Ghosted. Should I send her a gift to get her attention?
WINE AND ROSES
Only if you want her to send you a restraining order.
In rom-coms, grand gestures get you the girl. In life, they get you 60 to 90 days in county.