I have asked men out more times than I can count—digitally, that is. When I was single, I threw DMs out there like little power-up Super Mushrooms in Mario Kart.
If I saw a hot person on TikTok who lived nearby, I would leave a flirty comment on one of his videos, or find his Instagram and use a slightly cheesy but totally charming pick-up line. Most went unanswered, but I didn’t take it personally. They were strangers, so it was low-stakes and never that serious. One time, I even slid into an Olympic athlete’s DMs (and we talked for a bit, then it was a mutual ghosting situation).
Behind the safety of my iPhone keyboard, I was the most confident woman alive. (I’m a journalist after all, so my digital flirting skills are top-tier, if I do say so myself.) But, put me in a social scenario where I have to approach a hot man IRL? I was never able to work up enough courage to put myself out there.
In a 2018 survey from members-only dating app The League, one in three heterosexual relationships began by the woman messaging first. While a 2015 study from OkCupid found that women are 2.5x more likely to get a response than men are when they message first.
Those are super-promising statistics, so why aren’t we seeing more women making the first move? Turns out, there's a reality gap—a.k.a. a discrepancy between what daters want versus what they actually experience, according to Bumble’s 2023 State of the Nation Report.
For example, 54 percent of online daters surveyed said it doesn’t matter if the man or the woman starts a conversation with a match. And yet 40 percent said they agree that relationships work best when the man takes the lead, while only 11 percent said women should make the first move on a dating app.
Contradicting statistics aside, I still think you should ask out that hot barista at your fave coffee shop because life is short—do it for the plot! And these dating experts agree: Lily Womble, a feminist dating coach and the author of Thank You, More Please, and Chantal Heide, a life coach and relationship expert who has published over seven (!) books about dating, relationships and divorce. I chatted with both of them about how to become a more confident dater. Here are there tips:
Give yourself a confidence boost
Before you even think about making a move IRL, the first step starts with your self-esteem. Heide recommends meditating (which can help to reduce that “fight or flight” feeling), or doing things that increase your confidence and courage (like wearing your favorite pair of jeans). “This gives you the ability to confidently cross the room and engage with that person, instead of sitting in your chair wishing you could talk to them or desperately hoping they came to talk to you,” she says.
Embrace the awkward
Approaching someone you think is cute, with the possibility of getting rejected, is scary. It can be messy. It can be awkward. It can feel embarrassing. But making the first move is like a muscle you have to train—the more you do it, the easier it gets.
“If you're willing to feel awkward, then you become unstoppable in your dating life, especially in person,” says Womble. “This is about centering yourself and your desire as opposed to centering other people's thoughts about you.”
Start small by practicing eye contact, suggests Womble. Shoot a glance from across the room, then next time, try holding eye contact for a moment longer. If you’re feeling brave, throw in a little smile. “These are all significant wins that are building up your courage,” she says.
Heide also recommends doing the “hit and run” flirting technique. Introduce yourself with a smile, find something witty to say and start a short conversation. Ask things like: “Are you from around here? Do you have any restaurant/bar recommendations? What do you do? What made you choose that profession?”
Then, tell them you have to go, says Heide. Say you’ve got a meeting or an appointment you need to get to, but leave it open-ended: “I’d love to continue this conversation. How about I give you my information and we’ll get together for a coffee?”
What if you’re sliding into the DMs or messaging someone on a dating app? “I recommend using a deeper question that allows people who just want surface-level pen-pal conversation to see themselves out,“ suggests Womble.
Create 10 opportunities a day
“The more opportunities you create, the more chances you have to find the person that you want. It's the law of averages,” says Heide.
It’s easy to feel like you’re never going to find the right person, after another dating-app match goes nowhere, or a promising date turned out to be a total dud, or your third friend this week got engaged when you can’t even get a text back.
“You could find a relationship tomorrow, but I don't care about you finding a relationship. I care about you finding the best relationship of your life,” says Womble.
If you’re struggling to stay positive in your dating life, Womble suggests starting with these affirmations that will help build up that abundance mindset.
“It might be possible that I haven't met everyone yet.”
“It might be possible that I'm learning something new.”
“It might be possible that the right person is out there. I just haven't met them yet.”
Tap into your main character energy
When I tell my friends to ask for a guy’s number, a sentiment I hear them say is, “I don’t want to come across as desperate," “I want him to make the first move,” or “How will I know he’s actually into me if I asked him out first?”
But by never putting yourself out there, Womble argues that “you are setting yourself up to be the best friend character in your own dating life.”
This is what she calls under-functioning in dating, when you take your hands completely off the wheel and let somebody do all of the emotional labor of courtship because you think that will protect you from the people who aren’t right for you. But it actually does the opposite, Womble says. “You are just taking a back seat to your love story.”
Try an unconventional dating rule
Heide has garnered 875K followers on TikTok alone for her viral “no kissing for three months” dating rule. She argues that if you occupy the beginning stages of a relationship with acts of physical intimacy, you’re not actually getting to know each other. The men who are just interested in sex or a short-term fling will weed themselves out.
“If I occupy your mouth with my kisses, I'm not letting you talk. And if I'm not letting you talk, I'm not finding out who you are. And if I'm not finding out who you are, and we're kissing and having sex, then I fall for you because of the repetition of those behaviors,” explains Heide.
Untraditional, yes. But she might have a point. There’s a reason it works for all of her clients.
“You give yourself a chance to see the red flags,” she says. “We have decades of ‘kisses before we know who they are,’ and we now have a high divorce rate led by women because they're tired of the bullshit they put up with. This is turning a patriarchal dating structure to a matriarchal dating structure, which is required for a logical selection process.”
Remember: It takes two to build a connection
Becoming the main character in your dating life means showing up to co-create, says Womble. “That's why I don't think it actually matters who asks who out first. The right person is inevitable, and they will appear and co-create with you, so you don't have to do all that emotional labor on your own.”
Here’s an example:
“Hey, want to go out? I'm really enjoying this conversation.”
“Amazing. How about this time?”
“Great! How about this neighborhood?”
“I know this place in this neighborhood.”
“How about six o'clock?”
“I'll make a reservation.”
Don’t get ahead of yourself
When you hit it off with someone and exchange numbers, it’s easy to start fantasizing about the future. “What if this person’s The One?” I’ve often asked myself after a great first date.
But Heide encourages you to fight those (completely normal) urges and remain neutral. “Don’t create a story about them,” she says. “Then it’s disappointing if it doesn't come true. What you need to tell yourself is, ‘I don't know what I don't know.’ You don't have enough information about this person yet.”
Practice self-compassion
Say, you work up the courage to make the first move… and then you get rejected. Whether they just aren’t interested or they’re seeing someone, it still stings. How do you bounce back without letting rejection discourage you from putting yourself out there again?
Womble says that our fear of rejection is neurobiological—it’s not just a silly little insecure thought. “When we lived in caves, rejection literally meant being put out of the cave and dying of exposure,” she explains. “So, it makes sense [why we feel that way].”
Another way to shorten the time that you feel crappy about being rejected? Practice self-compassion. Your first instinct might be to push away the icky feeling of rejection and be hard on yourself because then you’ll move forward faster, but giving yourself grace actually reduces that painful window of time, says Womble. Go the extra mile and celebrate—with yourself or your favorite people—the fact that you took a risk in the first place!
And if all else fails, ask yourself, “Why do I care about people who are not in my life?” says Heide. And tell yourself: “I don't care if you don't want me. I don't want to be with anybody who doesn't want to be with me. The one who's the right fit is the one who will matter to me.”
One final thought
You never know where that first message, or first ‘hello’ IRL, could go. I made the first move with my current boyfriend. I came across his profile on Facebook, and I realized we went to the same college and had mutual friends. Turns out, he was my guy friend’s roommate in first year. He was so handsome, and he had “single” in his Facebook status, so I decided to message him on Instagram, “Do people still slide into DMs these days? 👀” And within an hour, he responded back, “I don’t know if they do, but I’m glad you did. How’s it going?” We’ve now been together for nine months, and I’m in the healthiest, happiest relationship I’ve ever been in.
How’s that for shooting your shot?
