I’m Bad at Flirting (and How to Fix It)

I’m bad at reading signals. Fine. That’s not too big a deal. Worse, however, is that I’m bad at giving signals. Or, rather, I am unaware of what signals I’m sending out. Am I failing to show interest? Do I accidentally deflect interest being shown to me? Am I showing interest that I don’t intend? This all comes down to a simple truth: I’m bad at flirting.

In this post, I analyze what makes me bad at flirting, both the behaviors and then the cause of them, in an effort to come up with ideas for correcting these issues. By the end of this examination, I will lay out some ideas for improving. I even have some events coming up where I can put these ideas into practice.

This blog post has been building for weeks. Erin and I talked about signals and flirting leading up to the blog about the ambiguity of male sexiness and how I don’t feel sexy. More so as we reminisce about the few times I knew I was being flirted with

We just listened to the Swinging Downunder podcast with special guests That Couple Next Door that was all about flirting. Apparently Cate and Kay are also bad at flirting. I will reference that episode a couple times, but I’m not going to quote it this time. If this topic is of interest, listen to it: It is informative, and it is funny.

If only we could all be like Darrell and Jay….

10 Flirting Behaviors

In that podcast episode and supporting blog post, the podcasters go through 10 behaviors that can help you identify if someone is flirting with you. Erin and I discussed the list ourselves during the car ride as we listened to the episode, so I decided to blatantly steal Cate’s list, and then Erin and I could write out our answers as to which of these behaviors we think we would exhibit to someone else if we were flirting.

Behavior Changes Around You

Shane: Nope.

Erin: Maybe a little. I am naturally very shy, so if I want to show interest in someone I push myself to be more engaging.

Their Body Language Changes

Shane: Nope. Though I recently started trying to not cross my arms when talking to people, in both lifestyle and vanilla worlds. It’s my natural, go-to standing position, but I understand in terms of body language science it is a sign of closing myself off. I still fall into doing so, but when I realize I’m doing it, I try to shift out of it.

Erin: No.

They Find a Way to Touch You

Shane: Hell no! But I am a hugger. 

Erin: No, but I have become more aware of other people doing this, and I think I can pull it off too if I make an effort!

They Tease

Shane: It’s in my humor to tease. It has nothing to do with flirting. So yes, I do this, but I do this to everyone.

Erin: No.

There’s Plenty of Eye Contact

Shane: Again, it’s in my nature to maintain lots of eye contact if I’m talking to someone. It’s actually an ADHD coping mechanism.

Erin: Yes. Of course I make eye contact in normal conversation, but if I am interested in someone I do make a conscious effort to hold eye contact a little longer.

Move Into Your Line of Sight

Shane: I have never done this.

Erin: No.

Body Pointed in Your Direction

Shane: Same as the eye contact, this is just how I talk to people. How do you have a conversation without pointing your body at them?

Erin: Yes, but I agree with Shane on this one.  Not sure how else you would have a conversation with someone.

They Always Laugh at Your Jokes

Shane: I laugh readily and heartily, sometimes at things few others find funny. I don’t intentionally laugh at other people’s jokes if they aren’t funny no matter how interested I am.

Erin: Yes.

Shane: Wait…really? Does this mean I’m not as funny as I think I am? You’ve just be fake laughing at my jokes all this time?

Fidget in Suggestive Ways

Shane: I fidget because I’m ADHD and restless. It’s never been suggestive. It’s not even conscious. If I’m around, you might feel the floor shaking cause my leg’s bouncing.

Erin: Yes, I do some of the stereotypical feminine fidgets.  Hair flip, lip biting, and the like.

Relaxed and Present

Shane: Relaxed and mostly present (again, the ADHD: my mind can go to some weird places really quickly), but I’m good at always looking present.

Erin: Not relaxed, but present.

Final Score

Shane: If we go by intention, 0/10. I don’t do any of these things to flirt with people. If we go by behavior other people see, then a 5/10, maybe higher. Shit, I’m sending out signals I don’t intend!

Erin: 4.5? But I think I mostly just come across as friendly. In most situations, people tend to see me as reserved (when really it’s that I am shy). So me making a conscious effort to be more outgoing I think results in normal friendly interaction as opposed to flirting.

Chatting Up, Flirting, Hitting On, Seduction: What’s the Difference?

Now to blatantly steal definitions from Merriam-Webster:

  • Chatting Up: to talk informally with (someone, such as someone one is attracted to)
  • Flirt: to behave amorously without serious intent; to show superficial or casual interest or liking
  • Hit On: to make especially sexual overtures to
  • Seduction: the act of seducing; especially: the enticement of a person to sexual intercourse

Given these definitions, the intensity of each seems to be in that order: Chatting up and flirting are informal without serious intention. Hitting on seems more specific and purposeful. Seduction is definitely purposeful and with the goal of sex. In talking with Erin about it, I said seduction is almost calculated: Planning specific words and actions to entice.

Does Intention Matter?

Many years ago I was hanging out with friends who had a toddler. Their little girl seemed enamored with me and was following me around from room to room. When I turned to talk to her, she would shy away. “Aw, she’s flirting with you!” they said.

That bothered the shit out of me. To me, flirting has intention. It’s purposeful, meaningful, and has an end goal (which might not be sex, but something).

Erin: When people use “flirt” in this context, I think they just mean that someone is showing interest, trying to engage with you. This does not imply anything sexual or creepy.  But this does add to the ambiguity of what flirting means and how to recognize it!

Yeah, but should they be using it this way? Merriam-Webster has amorous in their definition of flirt. For words to matter, we have to agree on their meaning!

Similarly, I have another friend who talks about how her son is such a flirt with the other girls in preschool. Dislike!

Apparently I’m a Flirt

Years ago, I was called a flirt by one of my friends. I asked some others, even Erin, if that was true, and they said yes. Boy was I gutted! I didn’t see myself as flirtatious—I certainly hadn’t meant to be!—and as such, I felt awful that I was flirting with women other than my wife. Apparently in her presence! When I apologized, she just shrugged and said that I had always been like that, and it was no big deal.

It was to me! 

Erin: Interestingly, I had no idea how much this bothered Shane until we started talking about it in the past couple of weeks. When I said he had always been like that, my thinking was something along the lines of “Are you a flirt? Well, if flirting means showing someone that you find them interesting and trying to make them laugh and feel good, then yes you can be a flirt.” I certainly never thought that he was intentionally making sexual overtures.

If Erin told me I was flirting with a waitress, I would feel bad because I wasn’t intending to flirt. I certainly don’t like the idea that I am putting out unintentional signals. It really bothered me when my friends said I was a flirt.

What Erin Means

However, after our conversations these past weeks, I’ve come to understand that Erin doesn’t think flirting necessarily shows intent or desire. If I’m flirting, that simply means I’m engaging in conversation in such a way as to elicit more conversation.

Just a couple nights ago as we had dinner out, I was joking around with the waitress, as I often do. I made her laugh, we had a conversation, she seemed well at ease joking back with me—we built a little bit of a rapport. Erin noted that I was engaging in friendly banter with her. She called that flirting. (Erin: I think that this type of thing can be seen as very casual flirting. The intent is to make someone feel good and to engage with them in an enjoyable way.  This is typically how Shane is acting when he is accused of being a “flirt.” It is clear to me, and I am pretty sure to the other person, that he is not hitting on them.) She knew I had no interest nor was I putting out any signals that there was interest other than all of us enjoying our time in the restaurant as much as possible. My only hope for our interaction was to make her night at work a little more bearable.

To Erin, flirting with someone doesn’t have to mean to convey sexual interest, so she was never threatened by me being a flirt.

So I shouldn’t be worried if she says I’m flirting. If I’m hitting on someone, however, I’d be in trouble.

What My Friends Meant

What makes me a flirt in my friends’ eyes? I’m friendly and engaging, yes. Random people approach and talk to me all the time. I’ve got plenty of stories about that happening. I don’t mind, and I will gladly sit and talk to strangers. I have a “welcoming aura,” or so I’ve been told.

And then mix in a propensity for suggestive jokes. If there is a way to make a naughty pun, I will make it. If there is a way to make something sound dirty, I do it. Because I’m always ramping up the sexual nature of a conversation, even subtly (Note from Erin: It’s usually not subtle), I’m a flirt.

Why I’m Bad at Flirting

Going forward, I’m using my understanding of flirting: A purposeful attempt to show amourous or sexual interest. By this definition, I cannot accidentally flirt with someone because I need intent. However, someone can think I’m flirting with them without me doing so. They are inferring what I’m not implying. (Words have meaning!)

I’ve Been Married a Long Time

Ours is not an uncommon story in the lifestyle: We started dating in high school. We got married out of college. Neither of us have experience dating other people. We never had a one-night stand. We were each other’s First Time for just about everything. I never developed the ability to show interest in women other than Erin because, before our foray into the lifestyle, I never wanted to show interest in other women. Sure, I could think that other women were attractive, but what did it matter? As a married man, I had no desire or intention to attract them.

I Don’t Think to Be Physical

I have never been a very touchy person except to my wife. Yes, I am a hugger. I readily embrace friends and family, male or female. However, it never occurs to me to touch during conversation. I see other guys do it to Erin, like putting an arm on her chair or around her shoulders. I then think, “Oh, right, I guess that’s a thing I could do….” It’s something that comes naturally to me when I sit next to Erin, but I would never think to do so on my own if next to someone else.

Except this one time, and it didn’t work.

A few weeks ago, we were at a club chatting with a group. Erin was on my left. A female from a couple we’ve played with was on my right. I had my drink in my left hand. I lowered my right hand to touch the other girl on her back. After maybe 30 seconds, if that, I took my hand off her back, switched my drink from my left hand to my right, and put my left hand on Erin’s back. Despite having had sex with this other woman—and more important, liking her, enjoying her company, and finding her attractive—I felt awkward having my hand on her instead of on my wife. I couldn’t do it.

Which leads us into….

I’m Uncomfortable Showing Interest

We’ve been in the lifestyle for a year and a half (this time), and I’m still not comfortable showing interest in other women. Yet. I’ve been conditioned through 14 years of marriage to only show interest in Erin. And when you factor in that we never dated anyone else, I never really showed interest in anyone else. I know her signals. She knows mine. Everyone else is a foreign language and forbidden fruit. Enticing, but outside my comfort zone.

I don’t have problems complimenting platonic, vanilla friends. But to interact with another woman in an effort to show and garner interest is still a strange concept to me.

I Worry About Erin’s Reaction

I am very guarded about the compliments I give and how I phrase things because I worry about how Erin will react to what I say to other women. Again, 14 years of conditioning: Not only should I not be showing interest in others, but she should be bothered by it when I do.

“That outfit looks great on you” is safer in my mind then “Damn, you look sexy!” I don’t want to create jealousy or a feeling of inadequacy.

Not because she’s particularly sensitive about these things. I haven’t crossed any lines. But that just reinforces the idea that being guarded is working.

Erin: Some of this is on me. Shane isn’t wrong that I might be…uncomfortable? Insecure? Maybe just thrown off because it is so different and unfamiliar?…by him showing interest in other women. That is something I am working on as we are slowly figuring out where our comfort level is—where our lines are—in the lifestyle. So his being this cautious is probably due, in part, to signals from me. I didn’t realize he was hamster-wheeling quite this much though, and I am working on challenging my own insecurities and helping him feel more comfortable.

Woot! Good husband points!

I Don’t Want to Offend

I worry, too, about how people might take my flirting. I’ve read so many articles about how women are tired of being approached and hit on by men, how every interaction could make them feel uncomfortable. I constantly second-guess myself.

Two more real-life examples for you:

The Grocery Store Girl

Back in college, I would shop at the same grocery store every Tuesday afternoon. It was a small store and usually dead at this time, so I often had the same girl at the check out. Despite being a regular there for months, I assumed that she had so many regulars in a week that she wouldn’t know me from Adam. She’d possibly recognize that she’d seen me before, sure, but we had no rapport.

One day, she had drastically changed her hair style. I thought it looked nice. I remember very distinctly thinking, “Wow, that new hairdo looks great on her! But I certainly can’t tell her that!” And I didn’t.

I was worried that even that simple compliment might have misinterpreted as flirting on my part, and I didn’t want to make her feel uncomfortable.

I told Erin about this at the time. She said I could easily have complimented her and been done. Grocery Girl probably does recognize me as a regular. She would get that I was saying something nice, and that’s where it would have stopped. The compliment isn’t flirting itself; the problem is when a compliment is used as an in to start hitting on someone.

As Erin said, I don’t come across as creepy, and I can read if someone is uncomfortable or unamused. I have much more practice at reading unamused than interested, after all.

The Grocery Girl probably would have liked hearing something positive about her new look.

Lifting Girl

I do not give unsolicited advice to people at the gym. I’ve often been asked by random people what I’m doing or how to use a machine or what my diet is like—welcoming aura!—but I do not initiate this.

One day, I saw a girl doing bench presses. She was finishing up her second set and her arms started shaking to get the weight up, but she went for another rep rather than racking the bar. I moved into position to spot her, just in case. She got it up without my help. I just smiled, nodded, and went back to my routine.

I have done this for several male lifters in the gym, and others have done it for me without me asking. It’s what we do: We make sure other lifters are safe.

I immediately started to question my decision. She hadn’t needed my help, so what did my decision to be there imply? Did she think I was suggesting she was weak?

Or worse, did it make her feel like I had been watching her the whole time? Had I made her uncomfortable because now she knew she was being watched in the weight room? I know lots of women view the free weights as “male territory.” Had I just made her feel unwelcome, or even unworthy of being there?

Yes, I am this neurotic.

We Lack Urgency

This is on both Erin and me equally, and it’s less of a flaw and more of just a rationale. Our goal on most outings isn’t to have sex with others; it’s simply to have a good time. We can do that through fun social interaction without it ever getting physical. It’s not a rule that we don’t play on first dates, but it is rare that we do.

We’re social swingers. We want to have a connection before we play. Not unusual.

But we never turn up the urgency. We’re not thinking that by the third or fourth date with another couple we should try to move things to the bedroom. Even if we decide we’re happy for things to go there, we don’t try to make it go there. We want it to happen organically.

I’m beginning to think that doesn’t happen. At least, not without one person willing to make the leap. After all, two people can move organically from sexy banter to touching and kissing to sex. Four people is a little harder because one couple will always have to go first, which means someone has to be able to take the lead.

This is the role Darrell and Jay take to great success, which is why they say they are good at flirting. They have the moxy to be bold.

The Reason Behind Me Being Bad at Flirting

Writing all this out was helpful. There are two main flirting roadblocks that I see:

I Worry Too Much About What Others Think

I overthink everything. Hell, I was heckled at our wedding for counting in my head during our choreographed first dance. I err on the side of caution when talking to women because I’ve heard plenty of horror stories about men making unwanted advances. Erin assures me I’m not the guy that women complain about. Not every compliment presents as a creepy come-on.

I need to trust that I come across as I mean: earnest.

I also need to accept that interacting with random ladies out in the vanilla world is different than the ladies in the lifestyle. Sure it’s easy to come across as a creep outside of the lifestyle, but women at clubs and meet & greets are expecting, even welcoming, a certain level of flirtation. I still need to be aware of signs (because it’s possible to be a creep inside the lifestyle!), but I should be able to trust myself not to go overboard in this realm.

I Haven’t Full Embraced Being in the Lifestyle

Half my reasons are as simple as this: I still behave like a monogamous guy. I’ve not gotten comfortable with showing interest in other women. I don’t feel guilty about it, but I also am not relaxed in the moment.

Oddly, I’m less hesitant about the sexual parts of swinging. I guess that’s because by the time we’ve gotten to that point, I have Erin’s permission. And that of the other people involved. During the build up to the sexy times, I’m still trying to navigate whether everyone is OK. As often as Erin and I finish each other’s sentences or text each other near identical messages at the same time, I’m not always sure what she’s thinking when meeting new people. We have to debrief after.

The lack of urgency fall into this section as well. Sure, we might be social swingers, but we are swingers. Let’s do this thing!

But Maybe I’m Not Bad at Flirting

No, wait, follow me on this for a moment. Part of my argument was that flirting is intentional. I’m bad at being intentional, no doubt. But my general social-interaction style rates pretty highly on the “he’s flirting” scale. Which means I don’t need to do much to improve. Relax, trust myself to read the signs, and be vigilant for moments to be more overt. Develop some moxy.

As I turned all this over in my head for the past few weeks, I had the thought that perhaps what I need are better situations in which to practice. I’m all about self improvement. Can’t get better at a thing without training.

Many of our stories involved clubs because Erin and I made the conscious decision to meet more people at clubs rather than couple-dating. We did the date-thing as our main vehicle for meeting people years ago (we were in the lifestyle years ago then took time off). We changed it up this time around because we really enjoy the sexy atmosphere of the clubs, and even if we don’t end up socializing much, we can have sexy fun with each other and still have a great night.

It’s more relaxed; less pressure. Clubs might be more difficult to score a hook-up and make a connection in a single evening, but that’s not our goal. We play the long game. Which results in us meeting and chatting with dozens of couples, but never even trying to connect with anyone on a sexual level.

However, by going in with no pressure or expectation for doing anything with anyone else, I’m missing that goal. I’m allowing myself to be passive.

Think it’s time to do some work.