Dating in the Lifestyle: Turning First Impressions into Lasting Impressions

My wife and I have enjoyed the lifestyle for several years. For those unfamiliar, the term “lifestyle” refers to those engaged in ethically non-monogamous relationships. It’s been fun navigating our feelings, opening communication to levels we didn’t know existed, and sharing experiences together we didn’t think possible. We’ve made amazing friends, fallen in love, been on incredible adventures, and checked many of the boxes on our sexual bucket list. It hasn’t come without some frustration though, and more often than not those frustrations are instigated by the lack of effort that men, in particular, put into their conduct and appearances. Women do a lot to get our attention and hold it, that effort should be reciprocal. It all starts with a first impression, whether that’s in person, via chat, a date app, or lifestyle site. As a whole, whether you’re in the lifestyle or not, we need to step it up fellas and I’ll address a few ways to do that in this article, Dating in the Lifestyle: Turning First Impressions into Lasting impressions.

When I was single, I really only knew how men dated or engaged with women through my own endeavors. I wasn’t privy to the conversations, flirts, or dating experiences women had with others in my gender because I didn’t have access to that sort of perspective. Sure, I’d meet women that were “fed up with dating” but I never truly understood that sentiment… until now.

Since opening our relationship up, I have gained a new perspective. A perspective more complete now that I have the ability to routinely observe the way men represent themselves not only to my wife, but to women in general on the variety of mediums we all use to meet new people. Hop on your partner’s swipe app sometime and browse the male profiles, it’s pretty despicable, no wonder they get fed up! Single guys, venture out of your comfort zone for a moment. Next time you’re with a girl friend that also uses the swiping apps, ask to peruse the male profiles with her. Wouldn’t hurt to know what your “competition” is right? I think you’ll be surprised at the level of douche-baggery going on.

We’re on a handful of lifestyle sites, a few of the swiping apps, and attend lifestyle parties, takeovers, meet and greets etc. where men should be representing the best version of themselves. Unfortunately, that just hasn’t been the case with a majority of men. Over the years I’ve observed a big disparity in the way women conduct themselves compared to the way men do. I hate to say it, but it’s my own gender at the lesser end of the spectrum when it comes to effort and tact.

“Whoa, shots fired bro! What kind of man bashing article is this?!” Don’t get your panties in a bunch fellas, I’m certainly not saying all men are guilty of this. In fact, we’ve met a lot of really great guys that do put in the effort. It’s because of them that I can offer my two cents on the do’s and don’ts of dating in the lifestyle.


How many times have you had the conversation with your spouse that sounds a little something like this?

“Hey honey, what do you think of this couple?”

“Well, she’s hot… but he’s a hard no”

Hey, I’m just telling it like it is, and if you’ve been in the lifestyle a while, you’re all too familiar with this type of couple configuration. Why do you suppose that is? How is it that there are so many attractive women putting their best foot forward, attached to guys that, frankly, just don’t seem to try? It makes finding those four way connections damn near impossible! I know single women in the lifestyle are called “unicorns”, but even more challenging to find is an evenly matched pair where the male half is bringing his “A-game” and matching the effort of his counter part.

Before jumping into what we can be doing better, let’s take a moment to consider some of the ways that women show effort. It’s important to understand a little more about the standard they are held to (and hold themselves to), in order to properly analyze our efforts on the same spectrum. Society has created a world for women that is more challenging, unfair, and to be honest, downright hypocritical. They deal with far more judgment than we ever have, and the truth is, most men wouldn’t last a day in a woman’s shoes. For as strong, secure and confident as we’d like to think we are, we aren’t tested in those areas daily to the degree women are. Understanding and acknowledging that fact is important, and every man should recognize it. Let’s take a moment to consider some of the ways women show effort.

 I’ll use my own beautiful bride as an example since I see her effort on a daily basis and she is a reflection of many other women in these ways. Aubrey’s physical appearance is important to her for a plethora of reasons. Of course, she wants to spin on this giant rock for as long as possible and be a good example for our little one. But she also does it because she has pride in herself. She wants my desire, the desire of others, to show up for us as the team we are, and to show the men that would court her, she respects her body; they should too. She goes through the rigorous routine many women do of putting on and taking off makeup. Eyeliner, plucking eyebrows, mascara, face creams, powders, lipstick, and painting finger/toenails to list a few. She stays on top of all that goes into maintaining her hair style (which is considerable). She wears perfumes, lotions, earrings, and all the other accessories women use to enhance their look and feel sexy. She works out six days a week and eats clean despite working and raising our child. Suffice it to say, the standard she holds herself to is impressive. This is the standard many women hold themselves too as well.

I could easily rattle off a dozen more things but you get the point. Women work their asses off (or on rather, depending how you look at it). These may be generalizations since of course not all women fit this description, but I think most would agree that women do a lot and are held to an incredibly high standard. The fact that society doesn’t expect men to do many of the things listed above doesn’t mean we should disregard all the effort they put into themselves. What it does mean however, is that we recognize that effort, and aspire to match it with our own.

Aside from appearances, women are also much better in general at making and holding a conversation. I date frequently and the vast majority of women I communicate with are good at it. Whether that’s in the form of text or in person, I rarely have a hard time conversing with them. Guys on the other hand… Aubrey is lucky if she meets one that can actually maintain eye contact let alone carry a conversation. Learning to communicate effectively is paramount and having a conversation should be fun and exciting, but more often than not I see men dropping the ball in their communication. It’s either short, uninteresting, narcissistic, or just non-existent. Also, men typically don’t get lazy, impersonal, or distasteful introductory messages from women like, “hru, wanna meet?” followed by an unsolicited picture of their genitals. You guys know what I’m talking about, it’s absurd, and men behave that way frequently. I see the ridiculous approach of these lazy slobs daily in Aubrey’s chats and direct messages. C’mon fellas, don’t be “that guy”! If you’re pausing to consider whether or not something is appropriate to send a woman, it probably isn’t… SO DON’T. Step up your game, learn to have a conversation!

 “So what exactly are guys doing that has you so irked?” Great question, I’m glad I asked. I could write a novel on the silly, ridiculous, and downright offensive behavior I’ve observed, but for the sake of this article, let’s keep it at those first impressions.


Dating sites and apps are a good place to start since this is where many of us seek out connections in this taboo lifestyle of ours. Regarding the lifestyle sites, what is the deal with so many accounts advertising as a couple, that don’t display the male half of the couple in the photos? Typically they include dozens of pictures of the female half, but either no pictures or only one photo of the male. And usually it’s an after shower selfie, in a mirror covered in toothpaste spots, a messy sink, and clothes on the floor in the background. Surprise! Women notice those things! If you’re on a site as a couple, do us all a favor, be equal participants. I realize many people value discretion, that’s completely understandable. Cover your tattoos or whatever you feel necessary for photos, get creative, but for the love of god stop putting your wife on display and using her as bait. Show people what they can expect from you. - Sexually Social

While we’re on the subject, use current photos on whatever media you’re engaging on! This means updating your profile when your appearance changes. Single guys using date sites, this applies to you too! Hey, quarantine didn’t do spectacular things for my body either, but I’m not going to keep photos posted of myself if they are no longer accurate. Ask any woman, they would much rather see a current photo of exactly how you appear today, than a photo you took ten years ago but still keep posted because you think you look sexy. Unless you plan on turning back time before you show up for a date, you’re setting yourself up for failure. Nobody wants to be surprised, because more often than not, it’s not a good surprise. If you’re filtering your photos… STOP! Do you have any idea how ridiculous it is to alter your appearance with the magic of technology? At the end of the day, the guy in the photos is what she’s expecting to show up, and unless you plan on growing antlers, a puppy nose, smoothing every wrinkle off your face or whatever other stupid filter you have on your photos, you shouldn’t be displaying anything other than your current appearance. Using filters is the epitome of cat-fishing someone and it’s not an attractive quality.

Don’t lie about your age. The thing that makes the lifestyle special is our ability to communicate so openly. We don’t play by the rules society has created for us and the power in our relationships doesn’t come from our ability to have sex outside of our relationships. What many don’t realize is that the real power many of us in the lifestyle possess in our relationships comes from our ability to be genuine, transparent, communicative, and above all, radically honest with one another. You don’t lie to your spouse, why would you lie to others? A number is arbitrary and shouldn’t matter. If you’re 55 and claim you’re 45, you aren’t fooling anyone, it’s pretty obvious. Tricking people goes against all the lifestyle stands for. Maintain your integrity and if people have an issue with your age rather than your appearance and behavior, do you really want to spend time and energy on them anyway? If someone is willing to lie about age, their integrity is shot in my opinion. What else are they going to lie about?

This be should fun, after all, we’re engaging in a relationship dynamic that is much more evolved than the standard narrative that was written for us by society. If you plan to write to someone, be intentional and fun. Guys that are impersonal and boring operate by casting a wide net. This is why they will end up either empty handed, dissatisfied, or at best, with a bottom feeder of their likeness. Rather, take a moment to consider who you’re writing to and put together more than a couple words to stand out. What things might you have in common? What piqued your interest? Why are you writing to this person? Express desire but do it tactfully. Writing to a woman and only opening up with, “how are you?”, is about the most boring, thoughtless, and in my opinion immature ways to reach out.  All that says is, “I wanted to open the door to communication, but I want you to start the conversation because I’m not confident in my ability to communicate.” Confidence and a direct approach can be a huge turn on for women, just temper it with humility and respect.

It all goes back to the golden rule, treat others how you want to be treated. How would you want someone to write to your wife? Single guys, assuming Mrs.Right is out there and any connection could potentially be her, shouldn’t you represent the best version of yourself in case this is the one? Personally, the sun rises and sets with Aubrey, I need her like I need oxygen and I’m insanely proud to be the object of her affection. I am always in pursuit of finding ways to make her happy. So believe it or not, I’m actually rooting for guys to really wow her when they reach out. I like when someone is over the moon attracted to her and desires her because I know how amazing she is. It turns us both on when someone else recognizes this and shows effort to know her. When she gets the bare minimum in effort, she will disengage. Life is short and time is our most valuable currency. Once it’s spent, it’s gone, no refunds. Why would she waste it on someone that doesn’t match her enthusiasm?

Dick pics… good lord where to begin? Men are so preoccupied with measurements and dicks they jump straight to it because they think that’s what a woman desires. News flash boys, they enjoy being pursued, flirted with, and when a man actually wants to know them for more than a romp in the sheets. Also, unless we’re talking about a size queen, most women aren’t as preoccupied with dicks as you may think. The majority of single guy profiles on most these lifestyle sites are always good for a chuckle. Ten different angles of your cock and none of your body or face aren’t going to get their engines going. Show more than that! What are your interests besides sex? How do you look with clothes on? Take off your hat and shades; show her what you actually look like. Display some pictures doing your favorite activity. And hey, if you still want to display your veiny triumphant 8th wonder of the world, have at it. Just realize, nine times out of ten, you aren’t doing yourself any favors. We all have dicks and at this point, it’s safe to say they have a pretty good understanding of what they look like. I know, it’s reaaaaally special to you, and you love showing the world, but not all women feel as proud of your dick as you do. Besides, that’s not what they see while you’re having sex. The condition your body is in however is something they see, touch, taste, and smell. Put more effort into those areas before you spend too much time worrying about your manhood.

Most lifestyle sights offer some sort of private photo album that you can place your most explicit photos in and share on a case by case basis. Sharing your private photo folder with someone should only occur after you’ve at least established a connection or are sending it in tandem with an introductory email. We often get sent access to private pictures from accounts that have never even attempted a conversation (even though our profile requests people don’t do this, red flag!) Again, this is a display of someone’s lack of confidence. So you can show us your most hardcore naughty photos, but can’t say hello? I’m supposed to do that for you? Give me a break! Do some homework on a profile before writing and sharing your photos. I’m always amazed at how guys write to us that have clearly not read our profile.

Depending on who created the profile or manages it, this next topic might not be specific to just men, but it’s applicable here so let’s get into it. Invest some time into your bio! Hey pictures are great and we should all be transparent in our appearance. We are after all on sites with a sexual undertone and looking to meet people for friendship as well as sexual experiences. But what else do you have to offer? What other information are you giving your reader about yourselves?  If I had a penny for every profile that looks like this, I could pave the moon in copper:

“Attractive couple that loves to laugh and have fun. We are only interested in no drama couples. Looking to make friends in and out of the bedroom. So don’t be shy, let’s grab a drink and see where things go”

BORING!!! Profiles like this literally tell the reader nothing.  Well, I take that back, it tells us the author(s) doesn’t really know what they are looking for. Let’s dissect what this bio actually says. “Attractive couple”? The readers will be the judge of what they think is attractive, but nice job finding a way to insert that subliminally. They like to “laugh and have fun”? Who the hell doesn’t? “No drama couples”? Whew thank god they included that because all the drama couples probably steer clear when they see that important nugget of information. “Friends in and out of the bedroom”? Ok, that’s nice, but also superfluous. It’s generally accepted people seek friendly connections, and if they aren’t, their bio should state they are only looking for a fling. “Don’t be shy”? Oh don’t worry, nobody is. Everyone is just bored to tears and wouldn’t want to waste time getting to know someone that can’t spend five minutes writing a bio that accurately represents themselves. “Let’s grab a drink and see where things go”… Thanks, we’ll pass. Getting a drink requires setting up a date night, possibly finding a sitter for many, spending money, and putting everything else on hold to give our time to meet. Why would anyone do all of that when they haven’t been stimulated mentally and don’t know anything about the author? If you’re ok rolling the dice with your time, have at it, but most people aren’t.

Am I being too harsh? I guess that just depends on how you value your time. Articulate some things about yourselves and what specifically you’re looking for. What turns you on? What turns you off? If you have any boundaries, this is a great place to state them! A boundary for you could be a deal breaker for someone else. For example, Aubrey and I aren’t interested in engaging with couples that have hang-ups surrounding kissing. Everyone has their reasons for their boundaries and I’m not one to question what works in your relationship, but that would be a deal breaker as far as play goes for us. Why not inform your reader of potential deal breakers to avoid wasting time on a conversation that won’t go anywhere? Talk about what you do for fun, this gives the reader an opportunity to relate on something besides sex. This all seems like common sense but anyone that’s on these sites knows exactly what I’m talking about.


Ok, I’ve harped on dating sites long enough; hopefully I expressed some ideas that resonate. Next let’s get into the ways we men are representing ourselves in person. Whether you’re meeting as a single male, a hall pass male on a solo date, or a man on a couples date, the principles remain the same. You should always put your best foot forward and put effort into representing the best version of yourself.

I already went over a handful of things women do to prep for these engagements. I get it; we don’t wear makeup, accessories, paint our nails etc. But there are plenty of ways to show up looking like you did your best to look good before meeting someone.

Hygiene is important. Women are meticulous about preparing themselves and look after every little detail in their own appearance, if you think they don’t also notice every little detail in yours, guess again. If you just got off work and have grease, dirt, or whatever gobbley goop you may have been into during the day under your nails, they will notice and it’s a huge turn off. Trim those shankers and clean under those bad boys! Show her you aren’t a slob.

While you’re at it, trim your damn nose hairs, shave your neck line, and groom whatever your facial hair situation happens to be. Brush your teeth, floss, and put on some cologne. If you look tired, worn out, and unkempt it comes across as lazy and you’re taking for granted all the woman has done to prepare for your date.

If the connection has been hot and heavy and you anticipate getting sexy together, trim your pubes! Hey, I know some women are into hairy guys, I’m not knocking that at all. However, nobody should have to lint roll their face and floss their teeth after giving their best oral performance just because you’re too lazy to manscape. Gross!

Put on some nice clothes and shoes. I feel like this shouldn’t have to be said but after seeing a man show up to pick Aubrey up for a date wearing dirty sneakers, old socks, worn out cargo shorts and a shirt that clearly displayed what kind of lunch he had around his stretched out neck line, I think it’s worth a mention. At the very least, make sure they are clean and wrinkle free. Give her Prince Charming, it’s what she deserves! So when a guy shows he doesn’t care about impressing her with his looks, despite all she’s done to prep, he’s already operating in the red. (The “Linus” I mentioned was sent packing if you were wondering).

Fellas, it never hurts to establish a “bromance” with the other male in the equation. Even if you’re a single male and maybe not even going to meet her husband, it’s always nice to reach out and introduce yourself. Make your intentions known, offer him a way to contact you should he need to talk to you, and tell him why you’re interested in his beloved partner. I know I always have more respect for the men that don’t treat these connections like transactions, but instead express gratitude for being given an opportunity to spend time with my soul mate. When I’m in the “other guy” role to couples I’ve met, I always like asking the male half what turns him on about me spending time with his wife. If you’re dealing with a couple, your aim should not only be to please the woman. You should also desire to make the male half of the equation happy with the arrangement as well and that takes asking them what their preferences are. It has nothing to do with your sexuality to want to mentally please another man. It’s about understanding the dynamic you’re choosing to engage in and making sure all parties are satisfied. These connections should only enhancing an already amazing relationship. Whatever your role, your goal should be the same, overall happiness and gratitude for everyone involved.

Lastly, be punctual, on time, and a gentleman. Make eye contact with a woman when you’re speaking to her. Ask questions about her life, family, and goals. Read her energy and don’t be the douche nozzle that continues making physical advances if she hasn’t made it apparent they are welcomed. If all you want to talk about is sex, you may still get it depending on how the rest of your presentation is, but probably not more than once. At the end of the day, women, just like men, like being desired for more than just their body. Find out what makes them tick, what turns them on, and look for ways to make her happy. Be chivalrous, make plans, and take initiative.

As we wind this down do yourself a favor. If you’re the male half of a couple, take a moment to recognize all that your counterpart does to look good and show effort. Are you putting in the same effort? If not, have no fear, it’s an easy fix. First, acknowledge her for what she does, I can guarantee she would love to hear it. To know that you recognize and validate all that she does and the effort she gives will make her feel great. Next, ask her what you can do to step up your game. Set aside your pride and ego for moment and accept some constructive criticism. She’s with you, she knows a woman’s mind, she can help you improve I promise. You can still be true to yourself and maintain your independence; nobody is asking you to be a robot, but why not get the inside scoop from someone who knows more about what turns a woman on than you do? It’s ok to ask her for help.

If you’ve made it this far, hopefully I got you to nod your head in agreement at least a few times. Again, there are tons of guys doing a great job and to those of you that always do your best, thank you! If you read some things here that raised your blood pressure, don’t take it personal. The point of this article, despite my often sarcastic humor, is to raise awareness regarding our behavior. We need to hold one another accountable for our actions, and inspire men in general to step it up. They deserve the best versions of ourselves.

2 thoughts on “Dating in the Lifestyle: Turning First Impressions into Lasting Impressions”

  1. Great article! Very informative and really nailed the bullet points that cross my mind often. I still don’t understand the phenomenon of the ill-advised dick pic, especially before meeting in person. Is this what our species has come to? I’m sure many of us hold advanced degrees from varying universities, so is this what education has boiled down to? The dick pic? Smh. Also found the part about conversational skills to be more than relative and absolutely germane to any form of dating. Has social media disabled or impaired the art of conversation? Anyway, well thought out and written. Thanks


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