I go on a lot of first dates, and women always ask the same basic question: “What was your last relationship like?” The truth? I’ve never had a relationship. I’ve never even had sex. I’m still a virgin. (In my 20s, I focused on my career, not dating.) When I get the relationship question, I lie like a rug. I act like I’m a player and reference my “many” past partners. I even mention an imaginary former fiancée. I feel shame about being a virgin and so inexperienced. I hate lying to women, but I’m afraid no one will want me if they know the truth. How can I stop doing this?
—G, 33, Los Angeles
Shame? There’s no shame in having no game. If you’re going to beat yourself up, do it for lying like George Santos, talking his way out of a speeding ticket. (“Sorry, officer, I’m late—I’m accepting the Nobel Prize in Physics for my discovery of entangled photons in physical cosmology. Yeah, that’s the ticket.”)
A man lies on a date because he fears the woman won’t like him for who he is. In your case, you tell yourself, “I’m a virgin, and that might mean I’m not enough for her.” So you wear the “player” mask, pretending to be the opposite of who you are.
No judgment here. I know all about telling big, fat whoppers on dates. Back in the aughts, when I first started working on my dating life, I met a woman named Lisa. I was way into her—smart, sexy, wickedly witty. I was schoolboy smitten, all but scribbling “Connell + Lisa” on my spiral notebook.
But I felt out of my league—like a Toledo Mud Hen trying to play in Yankee Stadium. What would a bright bombshell like her see in a bookish nerd like me? She was into outdoor adventure like SCUBA-diving and hiking. So I pretended to be the rugged, outdoorsy guy I thought she wanted.
Which is to say, I lied like crazy. On one date, I told her I was studying for my pilot’s license (lie), loved skydiving (double lie), and had swum with sharks in the Caribbean (triple-decker lie). I have a terrible poker face, and as I spun these yarns, my forehead turned into a Slip-n-Slide of sweat.
She friend-zoned me, of course. Because when you feel unworthy and pretend to be someone you’re not, women can tell.
Take it from a reformed fibber: Dishonesty hurts your soul—and it can hurt women. It’s a lose-lose.
Tell the truth, the whole truth. And I don’t just mean about your romantic history. Take off the “player” mask and lean into being real. There’s a deeper “truth” you’ve been hiding from women: the real you. Tell them that truth. Show them your humor, your opinions, your personality—and yes, when the time is right, your dating and sexual history.
Could some women be turned off by a notch-free bedpost? Sure. But it’s just as possible they’ll be into it. Candor can be an aphrodisiac.
Like you, G, my client Harvey was a workaholic virgin in his early 30s. On his third date with Stacey, the two were getting hot and heavy at his place. They hadn’t yet talked about sexual history. Mid-make-out, he paused and said, “Look, before we go any further, I want you to know—I’ve never been with a woman. I’m a virgin. I needed to be honest.”
Not only was Stacey not turned off—the vulnerability made her trust him more. Her reply? “I want to be your first,” she said. “And your last.” Then she led him to his bedroom.
Tell the truth. You are so much more than your romantic past. So much more than the number of relationships you’ve had.
You are so much more than enough.
On my last few dates, I got stuck in “interview mode.” I asked so many questions: “Where did you grow up? What year did you graduate? Where do you live?” At one point, a woman said, “I feel like I’m being interrogated.” How do I stop asking so many questions?
—Nicholas, 29, Indianapolis
Let’s bust a big dating myth. You might think “interview mode” is a bad thing, but it’s actually good—if you ask good questions.
Pummeling your date with boring, logical questions will get you breaking rocks in the Friend Zone. But ask questions that are fun, flirty, or thought-provoking (or all three!), and “interview mode” becomes your secret weapon.
There’s power in asking great questions.
I once had a first date with Rebecca, a costume designer for Broadway shows. I’m an introvert, and that night at the pub I didn’t feel especially “on” or charming. So, instead of faking gregariousness, I decided to play interviewer and let her do the talking. She opened up about her family, her work, her favorite shows. The conversation was about 75/25, her to me. I was good with that—I just listened and chimed in occasionally.
Here’s what shocked me: After we said goodnight and I hopped in a cab, my phone buzzed. It was a text from Rebecca: “I had so much fun tonight! You’re one of the most interesting people I’ve ever met!”
Me? Interesting? I’d barely said anything about myself! But because I asked good questions that she enjoyed answering, she found me fascinating. As the saying goes, “If you want to be interesting, be interested.” (Rebecca and I dated for a while and later became great friends.)
So, fear not the interview. Just make it a great one. Here are 7 fun, flirty, and revealing questions to ask on your next first date:
7. If we could be transported anywhere in the world right now, where would we go, and why?
This lets her imagine being with you as a couple—plus it’s a more vivid, engaging way to talk about travel.
6. Who should play you in the movie of your life?
It flatters her ego and gives you insight into how she sees herself. Be ready to answer this one too.
5. How did your parents name you?
Everyone loves their own name. I once asked a woman named Faith and learned she was named after the George Michael song. (Lucky for her it wasn’t “Monkey” or “I Want Your Sex.”)
4. Who did you see for your first concert?
Music = bonding. Be impressed if she saw Beyoncé. Fake horror if she admits to Nickelback.
3. What was the best day of your life?
This question takes things deeper—and women love talking about meaningful memories. Share your own answer first to give her time to reflect.
Mine? My dad’s surprise 85th birthday party, Halloween 2014. It brought me closer to my three sisters (we planned it together), and it was one of the last family events my mom, who was very ill, was able to attend. A perfect day of tears, love, and Reese’s Cups.
2. What was your first kiss like?
This light, innocent question adds romantic energy. Be ready to share yours first.
1. Do you like to see a first kiss coming—or do you like to be surprised?
All the earlier questions lead to this flirty closer. If she says, “I like to see it coming,” you say, “Well, here it comes.” If she says, “I like surprises,” you say, “Okay, then... surpriiise,” and go in for the kiss.
Don’t fear asking questions. Just ask the right ones.
I’m an accountant, and I love the certainty and mathematical aspects of my job. But when I go out to bars to approach women, I almost never talk to anyone because it’s all so uncertain. What if she doesn’t like me? What if her boyfriend wants to kick my ass? What if I get humiliated? Is there a formula I can use to make my accountant brain happy so I can actually approach?
—Seth, 29, Long Island City, NY
Seth, chatting up women at a bar is a lot different from crunching numbers on a spreadsheet. You’ve gotta let go of certainty. Embrace the unknown. You know the saying: Nothing is certain except death, taxes, and sucky Adam Sandler movies.
Dating coach Connell Barrett helps men all over the world find the women of their dreams. Connell has appeared on The Today Show, Access Hollywood, and more. Book a free call with Connell here.
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I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!
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