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For some people, flirting is just a part of who they are. It’s a natural expression. Flirting has two forms – the art of flirting in person and the more prevalent flirting electronically. But how do you express the full power of flirting? The first tip on how to flirt is for you to be authentically honest about your motivation for flirting and what kind of flirt you are. Are you an overt flirt, a sly one, or are you afraid to flirt? The second is to figure out the consequences of your flirting. And the third is flirting without attachment to a result. Learn more about how you can enjoy the power of flirting, some tricks and tips on what to do, and how to take it on if you’re on the receiving side of it.

This is a show on flirting, the power of flirting, and how much we enjoy it. It’s a life force for some. It’s energy, and it can get you in trouble. We then bring up some specific tips and tricks on how to flirt in person and then flirt on the text message, which is more flirting now on text message than ever before. Get some skills of how to be engaged and how to connect and how to bypass your fear, of how to flirt well and deeply. It’s about being authentic. It’s about being authentic with yourself and authentic with a person you are flirting with. We then bring Chris, who’s a great flirter in person, but put him on the phone and his mind goes crazy. We talk about his fears and some specific things and how not to get ghosted. For more shows, please visit us at TuffLove.Live. If you’d like to make a donation, please visit us at

060: How to Flirt

The show is how to flirt, one of my favorite topics. A few pieces of housekeeping before we get into the show. The first is a caveat or a notification. I’m in a down mood, and I had this heated discussion with Morgan on the topic of flirting. It was one of those all-nighters, even when you’re not talking, you’re still dreaming about the heated discussion. To let that, just to be authentic, just bypass and fake it. You’re a good liar. “You can get past this, and don’t show that,” but then another part of it was like, “This is Tuff Love. This is what the show is about. The show is about being real. This show is about being truthful,” and if something happens, that affects the show specifically.

We got on to a heated discussion around flirting, I’m going to talk about it. That’s going to be the first part of the conversation though. There will be some tips and tricks towards the end of it. The second is my good friend, Ben, asked me to talk about a charity that he’s supporting and it’s called Blind Connect. What Blind Connect is doing is in connection with Clear Choice. A course he’s taking is helping blind people with their lives. They’re taking donations, they’re trying to raise $85,000. It’s a 5123 tax ID. They have a 5123, so all your donations are tax deductible. If you’re interested to find out more about Blind Connect and you can contact Ben asked me for a donation and I said no because I was in a bad mood, but I’m going to change my mind. Don’t worry, I’ll make the donation. If you’re interested in getting in a good mood, the best way to do that is to give. That’s what TuffLove is for me. It’s an opportunity to give back round cuts by flirting.

Let me first talk about the perils of flirting, and that’s the topic of the show. The peril of flirting is that other people will be affected. I have an open and honest relationship with Morgan as those who have listened to the show can tell. It’s based on honesty. I’ve been doing a lot of writing working on my first book and working on a Lightning in a Bottle presentation, and the concept that I’ve talked about many times on the show is that withholding is lying. I’m a true believer in that. When you withhold information with you, you lie.

I have this agreement with Morgan to discuss the people I’m flirting with. There’s one visiting from Austin, a good friend of mine, someone who I’ve had interest in for years and unable to due to politics and we started flirting again. Every step of the way open, I have been honest around it. What happened was Morgan got triggered. I don’t want to go into her side of it, but her trigger hit my trigger. I realized that I wanted to stop flirting to maintain the sanctity of my relationship or to ensure that Morgan’s feelings are well-handled. There was this feeling of wanting to shut down.

Now Morgan is the flip side of that. She’s like, “I want you to have everything you want. I want you to have the ability to feel that sensation of flirting.” It’s been this back and forth between the two of how do you authentically be yourself and be in relationship, let them have their feelings, have your feelings connected to their feelings, and maintain your sanity. It’s not an easy yoga pose in any shape or form, but here’s my takeaway. Here is the thing that I’ve learned from this huge discussion is that flirting is part of who I am. It is an inherent part of who I am. If I shut that part of me down, then I’m stealing that from the world. I am robbing that part of myself in my expression. It is stopping me from fully being authentic in the world.

TL 060 | Power Of Flirting

Power of Flirting: Flirting is a way to express that part of you that wants to come out.

Flirting might not be part of your DNA, or it could be part of a small part of your DNA. It could be something you want to be but not want to be. There are different parts of yourself that wants to come out. My point is, what’s your relationship to flirting? That’s the first step of how to flirt well, is for you to be authentically honest about what kind of flirt. Are you an overt flirt? Are you someone who wants to be sly? Are you afraid to flirt? What are your motivations on flirting? What’s the inner game? What’s happening inside of you? I love to flirt because to me this is like a game. I’m not even interested in most of the time in step two, step two being a date. Step three, getting some nookie. Step four, a relationship. Sometimes, I just like to flirt. I like to flirt with men. I like to flirt with women. I like to flirt with everyone. I’m an equal opportunity flirter. I will flirt with anyone who I feel could enjoy that and get some attention, and then back and forth. The first tip about how to flirt is to authentically realize what kind of flirt and your motivations behind it. My motivation is it’s simply fun and it fills me up and it feels good. That’s the first step.

The second step is to figure out what’s the consequences of your flirting. Before, I thought my flirting was adding more energy to my relationship, adding more energy to my life, but what I’m finding is that there’s a limit. There’s a fine line I have to start paying attention to. There’s something I have to notice. There’s something more for me here to learn. I’m grateful for Morgan for the feedback to know that I can’t do the carte blanche flirting. I have to pay more attention in that aspect. Look at your motivations. Look what’s happening inside. Are you flirting to feel better about yourself? Are you flirting to have your self-esteem grow, or is it this desire to come out of your shell? Do you feel shy in your life, and you know that flirting will have you a place to express?

The third tip of flirting is I would recommend flirting without attachment to a result. People are sensitive and they’re aware. They know if you’re flirting to be friendly or connected or have fun, or you want something. When you have an end result, when have a goal, people can feel that. Are you looking for your life partner? Are you feeling sad and want to move out of your depression? Are you using that person to have yourself feel better about yourself? Notice these things. Be willing to truly look at the aspects of you around your flirting, and notice if you have a goal in mind, because that goal is definitely going to translate inside the flirting.

I did some research and I did some thinking about flirting and I realized that flirting now has two forms. There’s the in-person form, the art of flirting in-person, and the more prevalent flirting electronically. We’ve migrated a lot of our flirting to the power of the smartphone. We’ve definitely moved from speaking on the phone, because that’s what I did when I was a kid, dial those seven numbers, there were no area codes back then because we’re all in the same area code, dial those seven numbers, pick up the phone, pray that they answer the phone or pray that they don’t answer the phone or pray that their parents don’t pick up the phone. Wasn’t that the worst thing possible? I know for most of you youngsters who have their own cell phones, but having your parents answer the phone, “Hi, is Susie there?” The pitch of my voice would increase significantly when the parents would come on there. What happened was we had to call.

Everyone has their own personal devices, so we can flirt in our own secluded world and no one’s listening and no one’s noticing. There’s the flirting in-person and the flirting electronically. These are similar, but there are some differences that I want to talk about. I did some research on this on Google. It’s a great article. There’s a great wikiHow article with pictures that I thought was cool. I took some of my great ideas from them and I want to give credit where credit is due. Here’s some tips. This is a pragmatic show. Here are some tips on how to flirt on the in-person side.

The first is eye contact. Nothing expresses interest more than maintaining eye contact. Here’s the thing. If you get caught looking at someone, do not look away. Actually maintain eye contact. There’s this fine line between catching, “Hi, how are you doing?”to, “I am a stalker.” You have to be careful with that fine line. You go to a club, you go to a social situation, you go to a party, you go to a wedding, weddings are the best place in the world to flirt in my experience, but when you have an eye contact, pay attention. Look. If you get caught, most of us turn our face quickly and they catch you noticing. If you want to have the first step of flirting, it’s to maintain eye contact for another few seconds, and then smile.

For the men out there, the stoic who are taught that John Wayne’s stoic don’t-show-expressions is sexy, that’s true for handsome men in magazine articles, but if you’re staring and you don’t smile, what do you think you’re going to communicate? You’re going to communicate, lack of warmth and availability. Maintain eye contact. When you get caught, smile briefly and then see how they respond. If their eyes divert super-quick well, odds are that’s not going to be a target-rich environment. Odds are it’s having a no-show, but if they even maintain eye contact for a second and even smile for a second, that is a good sign.

After eye contact and smiling, the next step is to move your body towards that person. That could be the longest ten yards of your life. There nothing worse than you walking up to somebody who have a crush on and they’re usually surrounded by their friends. You smile, you walk up, and you know they’re wanting your approach and you can feel their approach and your body is going to turn on fire. Your genitals will probably move inside your body a little bit. Your heart’s going to beat faster, the sweat glands are going to start to move, but just keep moving.

Then talk and introduce yourself. You think about, “What’s my pickup line?” In Philadelphia, I worked with this beautiful bartender. She used to keep in the log book, the bar book, all our favorite pick-up lines. She must have 100. The best one I remember, this was 24 years ago or 23 years ago was, “Hey babe, where’s your space suit?” “What?” “Where’s your space suit?” “What?” “Because you’re out of this world.” Pickup lines. Don’t use a pickup line. Simply walk up and say, “Hi, my name is Rob.” Be willing to shake their hand, make contact, and just look them in the eyes and say, “Hi, my name is Rob.” That is the crucial first step. Be willing to be vulnerable enough to say and introduced yourself.

Then talk, show interest, ask questions, go slow, pay attention. You’ll know pretty quickly in the first minute if they want you to be there and if they don’t want you to be there. If they want you to be there, hold your body solid, be available. Try not to cross your arms. Try not to cross your legs. Be willing to sit and have your body be available. Be willing to actually connect. You can use things like leaning in a little bit closer and leaning out to show interest. You can use pregnant pauses now like that. If you can use pregnant pauses to bring them into your field and then out, be willing to lean in, but lean in deliberately. Don’t make them have their boundaries feel crossed. Just pay attention. Even a slight moving; we notice these little things. Slightly moving in will have them feel your interest.

Figure out what’s the consequences of your flirting. Click To Tweet

Answer their questions. Yes, there is a thought that you should put your attention to the other person, but also reveal parts of yourself so they know who they’re talking to. They don’t want to deal with a possible stalker. They actually want to know who you are, so answer questions about yourself and be vulnerable and be real. Don’t try to be anything you’re not. This is the worst thing. The worst thing is when you try to be something cool. There’s conspiracy of cool, where we all try to be cool. Don’t be cool. Don’t try to be that guy you saw on television that picked up the girl in the movie. Don’t do that. Be willing to authentically be who you are. If they want to be with you, it’s better to be who you are in those first moments so they don’t feel betrayed down the line. Be willing to authentically be who you are.

Don’t over talk, don’t speak so much and so quickly. Don’t have long run on sentences. Practice brevity. This is what we do. We speak fast and say the same thing over and over again and all of a sudden they’re there like, “That’s one long run-on sentence you got there, buddy.”Just speak. Speak in small, powerful, deliberate communications and don’t get ahead of yourself. Keep watching the flow. Keep noticing where the conversation is and authentically be real.

If you have a conversation and it’s going well, quit them early and what I mean by this is you know that you’re having such a good conversation and at the same time you could run it out, so be willing to quit the conversation early. What this means is something like, “I enjoyed talking to you. I have to go back to see my friends. Do you have plans on Saturday night?” Close the deal, be willing to say, “I’ve got to go, do you have the next step in our conversation?” Be willing to be vulnerable enough to ask. If that doesn’t feel right, you can simply say, “Can I have your number? Can I text you? Can we continue this conversation another time? Do you want to go out to coffee someday?” Be willing to take that conversation and move it to the next space. Be vulnerable enough to have it. That are some basic tips on how to do the in-person conversation.

How to flirt electronically is a similar but a different mean, because that’s on some level less pressure. We also have the ability of time. In-person, it’s a real-time conversation. You do have to stay in it. In the text messaging conversation, you have time to ponder your thoughts, and so it is a different vibe. I’m going to give you some specific tips on how to flirt electronically. Keep it casual. “How’s it going? How was your day? What was your favorite part of the day?” Keep it at a casual level at first, and then as they provide more and more information, ask some more intricate questions. Ask for more specific things, show interest, being willing to say, “I liked that. That excited me. What did you like about that?” Actually show interest. Be aware of when to ask for more interest. Be aware enough to notice what’s the right time to speak.

Show patience. Sometimes we’re in a conversation where it’s going well for the first seven or eight texts and all of a sudden we’re asking, “Do you like nude art? Do you take naked pictures of yourself?” Show patience. That person on the other line, you have no idea how they’re responding unless they overtly state it, so take your time. Be patient. Don’t overwhelm. Don’t give too much information. Just have the text message at a flow. If you’re paying attention, they’re going to provide you with enough information so you can tell. Notice the details of the text message, compliment, be vulnerable, be bold.

This is also important. Be mindful of esoteric statements or references. Do not quote your favorite anime picture and how you refer to the day to day. Don’t speak of some archaic science fiction movies from 1960’s. Be mindful, be careful, and keep things in present time. There’s nothing worse than a text flow when you say something obscure and they’re like, “What? What happened? What’s going on there?” Be mindful.

Lastly, it’s okay to leave them wanting a little bit more. You don’t have to play out your whole relationship on text message. Say things like, “That was an incredible conversation. I’m so excited. Can we talk tomorrow?” Or “What’s your day like tomorrow?”Or maybe, “Do you want to move this from text messaging to meeting in person?” A lot of people dating today don’t want to spend weeks texting, so it’s okay when you get that vibe to move it from the text message into the in-person experience.

Those are my basic tips of how to flirt. The main thing I want to get across from flirting is flirting is fun. Flirting is a life. It’s like a life energy for me. It can be a life energy for you. Flirt. What’s the worst thing in the world? The worst thing in the world is if you don’t have someone to flirt with, when you don’t have a crush, so do it. People are lonely. The worst thing that can happen if you flirt with someone is you give them a story to tell their friends, “This creepy guy was trying to hit on me at the Starbucks and it was the worst thing ever.” You definitely created experience in their day. That could be the worst thing, is that you give them experience, and underneath it some of them was like, “At least he flirted. I must be attracting something. I must therefore be attractive.” Give the gift of yourself, be connected, be vulnerable.

Live Coaching

Chris is on the line. Chris, I know, is a great flirt.

Hello, Rob.

How are you?

I’m energized. I’m shy because Summer is on the line.

Somebody to flirt with?

In this particular moment, like I feel full flirting. When I’m meeting new people in person at a kinky salon and totally make out with them and it is super-hot connection, and then we exchange numbers, and then it transitions to texting, I get flustered and fucked up. I go like, “I’m going to call you because I like actually hearing your voice and be able to catch the intonations.” I hate texting because I have almost a trauma around texting and being ghosted.

How do they respond when you say, “Can we talk on the phone?”

I’ve transitioned to where before I leave, I’m like, “I like to talk on the phone versus texting. Are you okay with that?” I’ve been getting good feedback and that’s working. For the times where I don’t preface that I’m a big phone caller, that’s where I get screwed or I screw myself.

Let’s explore a little bit what makes you so nervous around the electronic texting. What do you think is underneath it? Do you have any clues?


TL 060 | How To Flirt

Power Of Flirting: Flirting is not a win-lose proposition.

I’d say not being able to hear the tone and feeling like I will text the wrong thing.

It’s a fear of doing something wrong. When we did something wrong, what will happen?

I would be cast out of the flirting circle.

It’s not even just the one-on-one. You’re worried the reputation that Chris is an awful texter will permeate throughout the society, that Kinky Salon Society, and then you would be alienated.

There’s some of that.

I get that. I like talking in-person. I liked the intonation. It’s important as well. The skill of texting and flirting is something that’s required in today’s day and age. I know some people who don’t want to talk on the phone, they would actually prefer to do it over text.

It seems like a three-removed form of communication. If that’s preferred, that’s almost a red flag for me. It’s not going to be a good fit if they prefer to communicate twice-removed.

It’s totally a fine choice on your part. I totally respect that choice and I get it. To me it’s like having the skill set to have mastery. If you want to be a master flirt, you got to be able to flirt in all situations. The ability to dive in, to up your attention around losing intonation of the voice, you can hear intonation and texting. It’s not easy, but it is possible. There are times where you read a text and you’re like, “Wait a minute. The sensation in my body doesn’t quite match the words.” That’s them communicating somehow their intention. Isn’t the word ‘okay’ the worst text message ever? Okay is like, the genitals decrease some. It’s like the excitement decreases with ‘okay’.

Even my guy friends, I’ll say, “Want to have lunch? I’ll meet you at your house at 2:00?” He’s like, “Okay.” I’m like, “What is it about okay?” Sure, it is one step up from okay, but still is in the dark ages. It’s “Yes” that brings the excitement. Certain words, you can hear the intonation behind it. You’re good in person, especially at the parties, because you’re a good looking guy. Thinking about you and I’ve watched you experience is you have solid attention. That is the thing a lot of people can learn. When you’re in presence with someone, I actually can feel you’re not thinking about yourself, you have your attention on them. That is a powerful tool for you.

I feel the same. That’s not at all part of why I decided to be coached to. Thank you for your compliment. You are handsome, too.

Let’s talk about the part that you do want to be coached. Is it the transition from party to post-party? What happens from the environment of the party to less sensational venues?

I go to reach out either a day or two days later. Either I will not get a response or I will call and leave a voicemail and not get a response. Those have happened multiple times and leave me bewildered and wondering how I can do this better, because it seemed to be great in-person.

That’s the definition of ghosting. Ghosting basically is when you just bail. Everything’s going fine, you have a great conversation, and all of a sudden, you stop texting back. You stop communicating back. Ghosting is one of the biggest crimes in today’s society, especially with the ubiquitous swipe left swipe right that we can be like, “That was fun at the party. He was fun, but let’s see where’s the bigger and better deal? Where’s my next adventure?” Then we ghost each other and it is horrible. I am strongly against ghosting. It’s good to close the cycle and say, “I had good time with you at the party, but you’re not my type. I don’t think I want to continue this conversation,” which would sting for a moment. Why do you think are getting ghosted? What’s your hypothesis?

I’m getting ghosted because my form of communication post party is atypical. I imagine I’m perceived as weird when I leave a voicemail, expressing, “It was great to meet you and would love to see you again.”

Do you think it’s the content of the voicemail or just that you’re leaving a voicemail?

Just that I’m leaving a voicemail.

What would you think about having that first contact after the party actually be a text message?

I guess it would be much more like meeting in the middle ground.

I’m not fast in returning voicemails. I’ve gotten better because I’ve lost some business because of it and I learned a lesson about six months ago. I missed this call and then a bunch of other calls came in and all of a sudden it’s seven days later and they’re like, “We’re looking for a consultant, but if you take a week to respond to our call, I don’t think you’re the right fit.” I was like, “Shit, that’s totally right.” My point is perhaps it’s not you. It’s that they don’t recognize your phone number. No one answers their phone when they don’t recognize a number, and they’re not checking their voicemail until a couple of days later. Maybe there’s some part of them that feels that they haven’t checked their voicemail in a week. It could be that piece too. I’m just offering a hypothesis, there is no evidence of this whatsoever, but the point is maybe it’s you and you leaving the voicemail. Perhaps it’s their response to the voicemail.

In the world of text messaging, it could be a simple transition from the party to the phone call. You could do a bridge communication. Something like, “I had an awesome time with you at the party. I really enjoyed. Would you be up for a phone call via text message?” Then they can respond, “I’d love to.” Then you could say, “What’s convenient for you?” Actually give them the space, because a lot of us have busy schedules and we work or we have family or we have other relationships. Maybe that bridge text might be the key to move past this issue of those things. Once you are in connection, once you have that phone call, do you feel fluid or does it feel difficult out of the party scene?

If I’m in person or on the phone, it’s super fluid. If it’s in texts, I get super in my head. I over-read their texts. I misinterpret, I second guess, like “Am I texting something weird?”

If you do engage in texts, you should have some text practice sessions. You need a text practice buddy. We all need the text practice buddies. Maybe you need to ask the woman if you can practice texting, flirting with them, because when you’re in your head and you’re thinking, “Am I doing this right?” Or “Am I doing this wrong?”, then you’re not paying attention to them. They can feel that as well. They can feel that your attention is worrying, “Am I doing it right? Am I doing it right?” And not on the person. You can say in the text, “I’m nervous texting you. I prefer to be on the phone.” You can be vulnerable and real and it might diffuse some of the situation for both of youAll right buddy. It feels like we’re complete. Good luck. Thanks so much for being on the show.

Flirting is a way to express that part of you that wants to come out. Click To Tweet

You are welcome.

Let’s bring Chris, my friend.

I’m quite a flirt as well. I suppose I love flirting and I’m in a monogamous relationship and I still enjoy that interaction, that interplay, literally a play between individuals. I suppose most of the flirting you’ve been talking about is almost not quite gender-based, but it’s step to step. How do you flirt without needing to take it to the next level or enjoying the interplay of energy?

When you’re in a relationship, especially a monogamous relationship and you’re flirting, you have the danger of your partner thinking, “What the fuck is he doing?” And the person you’re flirting with, “What the fuck are you doing?” It’s best on some level express that you’re in a relationship before you start flirting. Set the playing ground. You can even be like, “I want you to know that I’m in a relationship and I just love deep connections.” You don’t have to use the word flirting, because that has connotation. “I’d love to know you more. I’d love to find out more about you.” You actually safeguard them in letting who you are, so they don’t feel betrayed or trespassed upon.

Sometimes you need to do that. Everyone I flirt with knows I’m in a relationship, and a significant relationship. People have the choice to flirt or not. Sometimes they’re like, “No.” I had this great lunch with this woman I was so attracted to. In the end she’s like, “I don’t want to do this. I don’t want to be engaged with someone who has a partner. I was like, “I totally respect that.” Being upfront, not trying to hide it, being authentic, is a way to take care of that issue. You might lose a flirt partner or two or seven or twenty, but it’s better than them feeling betrayed or then not knowing who you are.

One more question, “How did you get in trouble for flirting, Rob?” That blindsided me a little bit. I’m overt with Morgan. I’m honest with my flirting practice, and if I’m interested in a woman, we have a monogamous with guest star relationship, and that basically means that when we engage in alternative relationships, it’s together, which I’m happy about. It’s fun. I’m out in the world a lot of times by myself and will then get a text message and I’m flirting solo. There was some line that got crossed. There was some care I did not take in taking care of Morgan’s feelings and I was a little too intimate, not physically intimate, but emotionally intimate with this other woman that she didn’t know.

The lesson for me is to sometimes slow down and sometimes to check in more. Sometimes when that little voice in the back of my head that says, “I can flirt, I could do whatever I want. I’m a free human being,” but then to know the ramifications and the ramifications of how that would affect her, I need to pay more attention. The basic answer to your question is I got in trouble because I wasn’t paying enough attention to the effect of it, and that’s a lesson that I learned half a dozen times in our relationship with my miscues, and I will continue to learn and hopefully it will be a better and better flirter and a better and better partner to my love.

“Flirting is not a win-lose proposition.” Flirting is a way to express that part of you that wants to come out. Thanks for joining us on Tuff Love. I’m going to give you that email address for donations, This is for Blind Connect, and this is a way to help blind people in Las Vegas, Nevada. Please, if you’re interested in making a donation, you can also make a donation to me at There’s a way to give a monthly or a one-time donation to the show, As always, if you want more shows, please visit us at TuffLove.Live. Thank you so much for being with me on the show and thanks so much for allowing me to be honest and true. Hopefully it adds benefits to you and hopefully you can go out and flirts, get some more nookie, have fun, and engage in life. Thanks so much. Thanks so much for joining us for Tuff Love, a weekly live coaching call live from Los Angeles, California. For more shows, please visit us at TuffLove.Live. Thanks so much. I love you. Go forth and face the day.

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