Dating coach Connell Barrett gives examples of dating openers and conversation starters for guys.
Connell, once I’m in a conversation with a woman, I’m good! But it’s that first “approach” that just gets me so shoved in my head. I see cute girls everywhere–at the gym, at the bar, or a party—and I just freeze up. What do I say? And how do I avoid coming across like some kind of creep who’s bothering her?
—Ross D., White Plains, N.Y.
I feel your pain, Ross. The hardest part for me back in the day wasn’t talking with women. It was confidently knowing what to say to start a good interaction.
Let’s discuss the art of opening conversations with women.
Know this: When you open a conversation, it’s not as much what you say as how you say it. You need full commitment. An opener that tanks on Tinder (“Hi, how are you?”) can work great in person (that is, if you fully commit). Why? Because IRL she experiences all of your behavioral cues.
Your opener does not have to be clever or fancy—just good enough to get her to respond. I’ve begun conversations with openers as simple as these:
“You have great style.”
“How’s your night going?”
“I feel awesome today, and I had to share it with you.”
“What book are you reading?”
“Is this the coolest club around here?”
“Whoa, this line is long.”
“I’m sorry for your loss—but this is a really nice funeral.”
OK, that last one was a joke, but not the others.
When it comes to those opening words, sure, it’s a nice bonus if you’re clever or witty, but it’s just not necessary. Simple and clear is best.
My client Oscar was having a drink with friends at a Miami lounge when he saw Anastasia, a tall, intelligent pharmaceutical rep. He approached her, they liked each other, and later left the bar together.
The next day, his impressed (and envious) buddy asked Oscar what he said to Anastasia. What amazing opener did he use on her? Oscar explained, “I just said, ‘Damn, who are you?’ My vibe was, ‘I’m into you. You into me? Cool. Let’s get outta here.’ I’m a man, and she’s a woman. Why would it not be like that?”
Oscar used what’s called a direct opener. Every opener falls into one of two categories: direct and indirect.
“Going direct” means that your words and/or vibe convey clear romantic interest from the get-go. Here are examples of direct openers:
Hi, I saw you and had to meet you.
You’re absolutely adorable.
Wow. You’re gorgeous. Who are you?
I’m here to flirt with you.
Upside: There’s no chance of the friend zone. Whether or not she’s attracted to you, she’ll know why you’re talking to her. Lots of women love direct men, so it can ignite instant interest, like when I approached Brie. And it can feel freeing to shed weighty expectations and just be real with women from the start.
Downside: It’s a polarizing technique, so plenty of women will reject you right away. If she’s not available or just not in the mood, she’ll hold up a big, fat stop sign. Either sparks will fly or she will—as she walks away.
Quick Tip: Directness is not a license to be vulgar. If you go direct, don’t make it about her body, and don’t say anything about sexual acts. “You’re sexy” is about as blunt as you want to be.
“Going indirect” means that you don’t explicitly state romantic interest upfront. You might make small talk or give her a compliment that’s more friendly than flirty. You don’t hide your intentions; you just don’t lead with them. Here are some indirect openers.
How’s your night going?
I dig your boots/jacket/style.
Isn’t this song great?
How’s that book you’re reading?
Your hair looks amazing.
Upside: It opens the door to a lot more conversations since you don’t get as many blowouts. This helps you gain experience, build confidence, and talk to more women, which gives you more dating opportunities. In terms of starting interactions, going indirect gives you a much higher batting average.
Downside: Because the context is initially more Friend-to-Friend, some men get stuck in the “friendly guy” mode, which hurts their chances of creating a romantic spark. If you open in this way, you still need to flirt and be M-W fairly soon.
Quick Tip: After you open, within a minute or two, start to pepper the conversation with a flirty comment or two, such as . . .
“Wow, you have a sexy laugh. Anyway . . .”
“What do you do, when you’re not making handsome men flirt with you?”
“No way, you’re into [hobby]? You’re not just pretty. You’re actually cool.”
Try both, see what feels most like you, and go with what women enjoy the most.
So, you've used a dating opener, either direct or indirect, and now you're looking to keep the conversation going. It’s simple: Keep the conversation about you and her. (See Chapter 8 from Dating Sucks But You Don't, on great first dates.)
Now, if you used an indirect opener, you can talk for a bit about the icebreaker topic—say, the book she’s reading or boots she’s wearing. Then change subjects. A simple way to do that is to introduce yourself and shake hands. This lets you bridge to the next topic.
After a direct opener—such as “I had to meet you”—you have a couple of options. You can literally say whatever enters your mind, like complimenting her hair. Or, you can introduce yourself.
It’s fine to ask questions, but try to make them open-ended, rather than yes-or-no. And don’t forget Step 2 from my book: Offer Authentic Value. Talk about you. Make statements. Some guys interrogate women while sharing nothing about themselves. That won’t work.
Here’s a conversation I had with Nicole, a woman I approached on a cold January day in a grocery store. (My director’s commentary is in parenthesis.)
ME: Excuse me, miss. You look like the cover of J.Crew’s winter catalog. Super cute. (She was bundled up in a pink scarf and fuzzy white hat. This is a direct opener.)
NICOLE: [smiling] Oh, hi, thanks. I got the scarf for Christmas.
ME: Nice. How was your holiday? Get anything good? (That may sound like a boring question, but after a direct opener, you don’t need to do much. Normal, relatable chitchat is better than forcing funny lines.)
NICOLE: My mom gave me a spa treatment and a bunch of gift certificates.
ME: My dad hates gift cards. He’s such a Scrooge. But I’m the youngest of six, so I always get what I want. (I’ve offered info about me after asking about her. You want a balance.) I’m Connell, by the way. It’s a pleasure.
NICOLE: I’m Nicole! Nice to meet you. (Always introduce yourself.)
ME: So what do you do? Wait, let me guess. I’m gonna say you work in fashion. (It’s fun to try to guess what a woman’s job is. Games are fun!)
NICOLE: Not even close. I do social media for [company name], but we sometimes work with fashion brands. What do you do?
ME: I’m a magazine journalist. I write about golf. (I make a golf-swing motion. Using hand gestures can make you appear more charismatic.)
NICOLE: My dad loves golf! I’m not that into it, but I love to drive the cart.
ME: Just my luck. Pretty girls like you never play golf. It’s always the dads. (“Pretty girls like you” is another M-W statement. I’ve done more than enough to keep things flirty. We talk about salad for the next two minutes. Then, it’s time to go for a date! I still get nervous at this part, but I just go for it.)
ME: I have to go in a second, but I’m really glad we met. You’re really cool—even though you hate golf. (Just a little tease.)
NICOLE: It was nice meeting you, too.
ME: It would be nice to meet up when we’re not shopping.
NICOLE: Yes, I’d like that.
ME: How about a drink this week? What night is good for you? (Try to arrange the date during the interaction. Getting it on her calendar right away cuts down on ghosting and flaking because people like to be consistent with their commitments.)
NICOLE: I can do Wednesday or Thursday night?
ME: I’m free Thursday. Let’s do eight. Are you more into cocktail lounges or dive bars?
NICOLE: Hmm. I like both, but I’m down with cocktails.
ME: Okay, I’ll find a good spot and I’ll text you. What’s your number? (I take her number and stay for another minute. Why do I stay? If you bolt right away, she might feel that it was just about getting her number, like it’s a trophy. Hang in for another minute and talk about anything: the weather, spelunking, the Spanish Civil War. Don’t be a phone-number bandit!) Hey, it was great meeting you. I can’t wait till Thursday.
NICOLE: Thanks! You, too. I mean, me too! [laughs]. (She’s nervous and flustered. So dang cute.)
ME: You’re adorable. Bye.
When you get a woman’s number, send her a sweet text message the same day. (No need to wait or “play it cool.”) This solidifies the date, if you made one, and puts a smile on her face. That night I texted her: “Nice meeting you, J. Crew model, aka Nicole . . . I’ll text you deets for Thurs. 😉 —Connell”
Okay, let’s review this interaction through the lens of the Five Master Steps introduced in my book Dating Sucks But You Don't. Before I met her that day, I had been opening often, which put me in a social, outgoing mood. By opening directly and being me, I offered authentic value, which helped me make a connection right away. I decided to go for it and ask for a date. And in terms of appreciating something great, I was happy with my dating opener—and of course, landing a date.
Connell Barrett is an NYC dating coach, helping men all over the world find the women of their dreams. His book Dating Sucks But You Don't helps men learn how to connect with women authentically. Additionally, he hosts a podcast on how to get a girlfriend. He's appeared on Good Morning America, The Today Show, Access Hollywood, and more. Book a free intro call with Connell here.
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NYC Dating Coach Connell Barrett
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