You’re in line at a coffee shop. The woman in front of you glances at your order and says, with a little smile, “Bold choice.” Your mind goes blank, you say something polite, and the moment is gone. Then, on the drive home, the perfect reply finally shows up. If flirting feels rusty after a long marriage or relationship, you’re in very good company. In this episode I’ll show you what flirting really is (hint: it’s a rally, not a monologue), and give you a simple three-step way to do it naturally. You’ll learn what to do when a joke falls completely flat, how to tell if she’s flirting back, what playful flirting looks like over text, and how to turn good banter into a date. I also share one of the worst flirting attempts I’ve ever experienced, so you know exactly what not to do.
You don’t need lines, and you don’t need to be anyone other than who you are. Your stories, your curiosity, and your sense of humor are more than enough.
This is for good-hearted men dating after divorce or a long-term relationship who want a genuinely loving connection, not just another date.
How to flirt with a woman • how to flirt naturally • flirting tips for men • how to flirt over text • dating after divorce for men • flirting after a long relationship
Links and Free Resources:
1. Free Guide: “Why You’re Not Finding Love (And The Inner Shift that Changes Everything)” → https://datingcoach.
2. Dating After Divorce? Get The Relationship You Want with Dating Mastery for Men → https://datingcoach.
3. Audio Masterclass: Relax and Enjoy Conversations With Women Here → https://datingcoach.
So let’s say you’re standing in line at a coffee shop, and a gorgeous woman that’s in front of you turns around, she glances at the coffee order in your hand, and she says with this little smile, “Ooh, bold choice.” And in that moment, you’re going, “Oh my God, is this gorgeous woman flirting with me?” And your brain just completely empties.
But you like, you need to do something, so you kind of smile back at her and you’re like, “Oh yeah, it was pretty good.” And you feel awkward, and the moment’s gone. And then as you’re driving home with this coffee, the perfect reply to this gorgeous woman pops into your head. Now, if this type of situation or scenario has happened to you, you’re in very good company, especially guys if you are kind of single again after a long marriage or a relationship has ended.
Flirting can feel like a language that you used to speak but you haven’t practiced in years. So today I’m gonna give you a simple three-step way to reengage with flirting really naturally, what to do when a joke [00:01:00] falls completely flat, how to tell if a woman’s actually flirting back with you, and what this looks like over text versus, you know, in real-life situations.
I’m even gonna share one of the worst flirting attempts that I’ve ever experienced so you know exactly what not to do. Now, welcome to this channel. My name is Kimberly Hill. I’m a dating and relationship coach for men. I support good-hearted men to attract deeply loving relationships and go on to maintain those relationships.
Now, there’s two things I wanna briefly mention before we dive into today’s content. The first is if you are struggling with dating, you’re finding that you’re attracting the same type of relationships over and over again, they’re not feeling good, or you’re not quite sure why things aren’t lining up for you, I have a free guide that I created called Why You’re Not Finding Love.
It’s nine chapters. It’s quite direct, and it’s gonna help you understand why you might be feeling so frustrated or struggling in the dating space. So go ahead and grab it. It is completely free. Now- If you’ve been watching this YouTube channel or listening to my podcast for a while, and [00:02:00] you’re actually at the point where you’re going, “You know what?
I really wanna… I wanna be intentional about dating. I wanna do something about it. I really am here because I wanna find and attract a healthy, loving partner and go on to have a loving relationship,” then I have created a self-paced program called Dating Mastery for Men that is going to help you achieve exactly that.
It is not a program for everybody. It is a program for men who take this part of their lives very seriously, even though they wanna have fun with it, um, and are really ready to show up, do the internal work, as well as, um, be guided on how to build a healthy, uh, online dating profile and to truly attract the type of woman that is going to get them the relationship they really wanna have.
So if you are serious about doing the work to achieve those things, then please check out Dating Mastery for Men. Now, let’s dive into what really is flirting because, you know, it’s, it’s not… It ain’t pickup lines, and it isn’t just innuendo. At its [00:03:00] heart, flirting is a playful back and forth that sits somewhere between friendly and romantic, and it makes a conversation fun and enjoyable, and it quietly lets a woman know that you are interested in her.
And here’s the part that’s gonna take the pressure off. Flirting is very much a rally. It is not a monologue. You do not have to be brilliant. You toss something light over the net, and you see if this woman hits back. And there’s actually a reason behind why this lightheartedness, uh, works because People who study adult playfulness have found it’s one of the traits that we value the most in a partner because it signals things like warmth, good humor, that you’re a safe person to be around.
We don’t tend to have fun with people that we’re not comfortable around. So when you are playful, you’re telling a woman a lot [00:04:00] about who you are. And here’s, guys, here, guys, is why you might be better at flirting now in your 40s, 50s, 60s, or 70s than you have ever been. Because flirting is made of small, playful moments, a light observation, a gentle tease of a woman, a funny little story or anecdote, and all of that comes from what you know and what you have lived through.
So you’re at a point in your life where you actually have decades of stories and opinions and experiences to draw upon. So the more enrichment you add to your life, the more content you’ll have to play with in flirting. Your life and your experiences and your knowledge really become your flirting material.
So I wanna give you a simple way to think about flirting. I don’t often kind of break things down into steps, but I think in this case it can be helpful. The three steps are notice, [00:05:00] play, and reveal. So when we talk about the noticing part, you are noticing something specific about a woman you see or the woman you’re on a date with, or about the moment that you are both in.
Maybe it’s her coffee order, the book she’s holding in her hand, something funny that’s happening around you. But noticing also means whether, noticing whether a woman is even open to this kind of conversation right now, and I’ll tell you a story about this one. Now, when I was back living in Vancouver proper, I went to the gym.
I was in the middle of a workout. I had my earbuds in. I was very, very focused on my routine, and A man walked up to me, he looked very flustered, he was almost panicked, and he waved at me to take my earbuds out. And of course, my adrenaline started going. I’m thinking, “Holy shit, what is going on? What’s wrong?
Is the gym burning down? Like, is something happening?” So my immediate reaction to this man [00:06:00] approaching me was adrenaline and a bit of panic. And then his line was that he had to come up and tell me that it was so inappropriate that I look so good while working out. Now, part of my brain was laughing at the humor of that comment, and I know he meant it as a compliment, but his approach startled me.
My body was already in alarm mode, so instead of feeling flattered and disarmed and ready to have an engaging conversation, I actually felt frustrated. My face was red. I wasn’t open to this conversation with him at all. I just wanted to get back to my workout. And there’s a little lesson here, right? When you approach a woman with no context in a way that can create panic or alarm, you are likely to lose her interest before you’ve even begun.
In this case, I was very focused. I had my earbuds in, and this man made a comment about me, and I wasn’t open to receiving it, and I’m typically very [00:07:00] open to receiving, um, you know, talks with strangers and compliments and all these types of things. So what I’m saying here is I want you to notice the moment.
If you… Especially if you’re wanting to flirt with a woman that you’ve never met or not even on a date with, or even that you are on a date with, you wanna assess, is she relaxed? Is her body posture open to you, or is this woman, like, occupied, busy, and focused? Because flirting always lands best when a woman is already feeling at ease.
So this is notice. Okay? Now we move on to what’s called play. So once you’ve noticed something about her or about the environment, play with it lightly. Tease her choices, but never her body. Say she orders at this coffee shop… What do people order these days? I don’t know. A caramel oat milk latte with extra foam, okay?
You smile and you say, “Oh, I took you for an all-black kind of coffee girl.” It’s light. It’s about something she has [00:08:00] chosen, and it quietly tells her you’re forming an impression of her. Now this woman gets to play back. “Oh, really? And what else did you assume about me?” And just like that, you’re flirting.
Okay? The third step is reveal, and this part is where you reveal a little something about yourself. So flirting isn’t just about teasing her. It is, but not just. It’s also letting her see you and understand you, too. So let’s say you’re on a date with a woman, and the topic of hiking comes up, which is very, very common in the Pacific Northwest.
So she mentions she’s into hiking, and you say, “Okay, full disclosure, last time I went hiking, um, and camping, I pitched my tent in the dark, and I woke up in a ditch. So you probably are gonna need to be my hiking and camping guide.” Okay, now she knows something real and funny about you, which means you’re letting her see your interest.
You’re not [00:09:00] too egotistical or rigid to tell her a story that’s somewhat embarrassing or self-deprecating, and it allows her to be disarmed and play back with you. Now, revealing also means letting a woman see your interest in her, which could be a specific comment like, “I really love how you light up when you talk about your work,” or at some point just saying a simple, “I’m really enjoying talking to you.”
It’s clear, it’s warm, it’s confident, and you are revealing something. So notice, play, and reveal. Those are the three steps to enjoying flirting. That’s really all it is. Now, what can happen if you’re doing that, but let’s say you take it too far, or your joke falls flat? And I’m, I’m the queen of this, right?
Like I, I love a little sarcasm. I love a little witty banter. I lived in Australia for many years. It’s really part of the culture there, but sometimes I’ve taken it too far. [00:10:00] Okay? Or sometimes you guys might take it too far when you’re teasing or joking with a woman, and maybe she gives you this kind of polite smile and a nod, and you know, oh shit, this didn’t land very well.
Well, here’s a secret. Don’t panic. Do not over-explain yourself, and definitely don’t apologize five times. Don’t, you know, back down completely. Just own it with a smile and say, “Okay, that was a lot funnier in my head. I’m sorry.” All right? It’s just a easy self-awareness, a little correction. It’s genuinely charming.
Just because you’ve made one little error or mistake, it doesn’t need to ruin the whole evening or ruin all of your connection. It just shows that you’re comfortable with yourself even when you make a mistake, and a c- comfort is a very attractive quality. So in, honestly, a joke that flops followed by a calm and good recovery can land better and help your connection more than a joke that just worked in the first place.
So- [00:11:00] Now, how can you tell if a woman’s actually even flirting back with you? ‘Cause maybe you guys are going, “Okay, well, I’m doing these things, but is she, is she buying it? Is she having fun with me?” And all you wanna do is look for a few things, guys. Is she teasing you back? Right? Does she keep the joke going a little bit, or does she reference the joke a little bit later on, right?
She’s gonna ask you personal questions. She’ll find reasons to stay in the conversation a little longer. But if a woman is giving you short answers, she’s looking away, she’s turning back to whatever she was doing before, like you, maybe you approached her in a cafe, you said something funny, and then she’s, like, back to reading her book, okay?
That’s okay, too. This is not a verdict on you. It’s just not the moment for it or not the woman for it, so you just ease off warmly, and you let it go. Now, I also mentioned I was gonna address what it’s like to flirt with women on these wonderful little devices because, you know, nowadays a lot of flirting is gonna happen [00:12:00] over text, you know, before you even get to the date.
And honestly, it is the same three steps, just a little bit shorter. You’ll notice something from your conversation with this woman. You’ll play with it a little bit. You’ll reveal a little bit about yourself, um, and that might look like this. So let’s say the day after, um- Ah, let’s see. Okay, so let’s say you’ve already exchanged numbers with this woman.
You had that little banter at the, at the café. You might send her a message on text saying, “I headed out to order my morning coffee this morning and thought of you. I got a black one obviously. Someone has to keep the standards up,” right? Whatever. Okay, it’s playful, it calls back to something that you have shared together, and it gives her an easy, fun way to reply.
Not all texts need to be serious. They’re just little drop-ins to keep the kinda ember of connection or the ember of flame of connection alive between the two of you. So you don’t need to send multiple texts in a row. Just remember that texting is very much a warm-up, not the main event. [00:13:00] But texting is just follows the same process, usually just a little bit shorter.
Now, where flirting leads, because the point of flirting isn’t to banter endlessly, right? ‘Cause if that’s the case, eventually someone goes like, “Okay, maybe this is all it it, it is.” The point is to build enough connection with a woman that asking her out feels like a very natural next step. So it’s you’ve had enough fun in the conversation that you can honestly say, “I would have fun over dinner with this woman,” right?
If you don’t know enough about her to know if you could even have, like, two hours of a good time, maybe you’re not ready to ask her out. So once there is good rhythm between you, you take it there. “I’m having so much fun talking with you, like, I haven’t had this much fun in a while.” Makes her feel special.
“I’d love to take you for a proper coffee. You can order whatever ridiculous thing you like” if you wanna keep the humor going. Okay, it’s playful, it’s clear, it’s easy for her to say yes to. Now, of course, as you guys know, there’s a [00:14:00] few things you wanna be mindful of or avoid with flirting, and that’s suggestive comments too early, teasing a woman’s appearance.
You never wanna tease or be teased yourself about something you can’t change about yourself. So if someone l- drops a comment in my, you know, my YouTube channel that they don’t like my face or my nose, there’s nothing I can do about it, so sorry, right? You don’t wanna tease someone about something they can’t change about their self.
You also don’t want to lead with your resume instead of your personality, and a lot of people do this when they get a little uncomfortable. They don’t know what to talk about. Um, and you also don’t wanna ask so many questions in a row that it starts to feel like an interview, right? Again, this flirting concept is, you know, you know, some- something light goes over the net, she f- you know, she hits it back to you.
So here’s a little practice for you guys this week. One day, to some woman, make a playful, warm observation to her. Maybe it’s a friend, maybe it’s a neighbor, [00:15:00] uh, maybe it’s a gal you ran into at Home Depot. I don’t know. It doesn’t have to be romantic, okay? That’s not the intention i- initially. It’s just playful.
It’s the part of you that’s easy to reach. And whenever you’re flirting, ask yourself two quiet questions. Is this person kind of playing back with me? Or the other question is, am I enjoying this, or f- or do I feel like I need to perform for this person? Because if she’s not playing back, you just ease off, and if you’re performing, slow down and get curious about this person instead.
So the next time a woman says something to you out in the wild and you usually would draw a blank, now you’re gonna know what to do, okay? Notice, play, and reveal. Read the moment. Keep things light. And this is honestly why, guys, even if you feel like I- you haven’t had practice flirting for 20 years ’cause you’ve been married, you have [00:16:00] tons of life experience, wit, comment, and things to draw upon to have some fun.
You have to take the pressure off yourself that even little bits of flirting with new people has to always go somewhere very serious. Just enjoy this kind of playfulness and humor in life with all sorts of different people, which sets you up for success when you are flirting with someone that you feel like the stakes are a little higher, right?
You don’t need to memorize lines, okay? You don’t need to be, uh, anyone other than who you are. Just bring your stories, your curiosity, and your sense of humor, and genuinely enjoy the women that you’re flirting with in front of you. So I hope today was helpful. I hope there was something that you could take from this video that’s tangible for you.
And of course, I wanna thank all of you guys for your valuable time today, and of course, I’ll see you all next week. Ciao.
