I think I might be a Playboy. Is that a bad thing?
December 3, 2021 10:27 AM   Subscribe

I know there are negative connotations to this but hear me out.

So I've basically been struggling for a long time in relationships. Most of it has been a struggle between what are the things I enjoy Vs. what is expected of me in society. I've really really tried the whole staying with one woman for the rest of my life. I even committed to a marriage which only lasted a year before she broke up with me. Now I no longer want to fight it.

I work hard to have a certain lavish lifestyle, full of adventures and memorable moments. I like to date women, and it doesn't have to be multiple. In exchange of their company I provide them security, money, gifts, I basically want them to have one of the best times of their life. I respect them and let them know upfront that I'm not looking for anything serious.

The way I see it is that 50% of this women divorce anyways and many of them have lacked that enjoyment and adventure in their life. I want to give them an experience they won't forget, I want them to at least in the moment feel like complete bliss and adoration before some of them venture down the path of a miserable marriage to someone else.

Am I being too selfish? Am I an asshole for wanting these things? As I mentioned before, I do work hard, and try to give back to my community. I just don't see myself being in a marriage raising a family.

I'm curious to know what you all think, or if you know any other playboys out there, or if you are one! I'm also interested in knowing if there is a kind of code of ethics for Playboys that they should adhere to.
posted by red47Apple to Human Relations (57 answers total) 6 users marked this as a favorite
It sounds to me like you have tons of justifications for your behavior; if they're no longer convincing you, you must look within.

If the question is whether it's okay not to want to get married or have a family, of course it's okay not to want to get married or have a family.
posted by babelfish at 10:35 AM on December 3, 2021 [17 favorites]

Why do you think women need gifts to want to hang out with you?
posted by chesty_a_arthur at 10:35 AM on December 3, 2021 [13 favorites]

Response by poster: I never said they needed gifts to hang out with me. I enjoy getting them gifts just for fun.
posted by red47Apple at 10:37 AM on December 3, 2021

If you are honest and upfront with women, I don't see anything wrong with not having serious relationships.

But this post makes me sad and I don't know what you are getting out of this.

I'm not one to come in to ask metafilter and say "get therapy" but I think you might really benefit from it.

I am older, and I will say, I don't know many happy, old playboys.
posted by beccaj at 10:39 AM on December 3, 2021 [11 favorites]

I think this is just called dating.
posted by chesty_a_arthur at 10:40 AM on December 3, 2021 [40 favorites]

The way I see it is that 50% of this women divorce anyways and many of them have lacked that enjoyment and adventure in their life. I want to give them an experience they won't forget, I want them to at least in the moment feel like complete bliss and adoration before some of them venture down the path of a miserable marriage to someone else.

So your modus operandi is to shower women with grace and favour so they remember you well when they leave you and move on? In your fantasy, are you showered with goodwill at a result of this? Do they come back to you in regret and shame and do as you say to fall into your arms again? Do their husbands let their guard down and let their wife cultivate a relationship with a benevolent sugar daddy who asks for nothing but... What? The questions are not likely to get easier.

Another question is why do these women need to be saved by you if you expect to leave them behind? You seem very consumed by patriarchal thinking.
posted by parmanparman at 10:40 AM on December 3, 2021 [32 favorites]

My kneejerk reaction is that this sounds kind of immature and naïve -- there is a LOT of greenfield between serial dating and having exciting adventures and miserable married monogamy.

But yes, there are lots of people who don't want to get married or be in long-term relationships or raise children and no, no one really cares as much as it sounds like you think they do. It actually sounds like you care about this idea a great deal and are struggling to reconcile yourself to acting in ways that don't support it. I suggest that you really think about how you define and seek out the kinds of relationships that you prefer.
posted by sm1tten at 10:41 AM on December 3, 2021 [30 favorites]

Didn’t you recently go through a divorce? I I think you’re just kind of processing that whole thing right now. It’s fine.
posted by cakelite at 10:47 AM on December 3, 2021 [16 favorites]

I don't see anything selfish here or anything I feel compelled to tell you to stop. If you're having a good time and they're having a good time then what's the problem? It does sound like you feel vaguely guilty about something you can't put your finger on, and that's something a therapist can help you work through.
posted by bleep at 10:49 AM on December 3, 2021 [8 favorites]

Look into "relationship anarchy" - which, in broad strokes, is the concept that you don't have to get onto a "relationship escalator" (i.e. - dating, exclusive dating, marriage, family) when you start seeing someone.

It is not uncommon in the polyamory community, so though you seem to prefer serial monogamy (since you wrote that you don't want to date multiple women at a time), it is not exclusively (heh) for polyamorists.

The main takeaway - always be clear what you are seeking and what you are offering, and you will likely find those who are compatible with that.

And never let anyone tell you what you want - you're the only one who knows that.
posted by birdsquared at 10:49 AM on December 3, 2021 [7 favorites]

Sounds fine to me as long as no one’s expecting more than you want to give. Serial daters aren’t that rare, are they? But why are you questioning it - have people been unhappy with you or something?
posted by acantha at 10:50 AM on December 3, 2021 [6 favorites]

The rule of the game is informed consent. If you are honest with your partners about what you want, and they're into it, then you are morally in the clear.

You should get STD testing regularly to make sure you aren't spreading diseases.

And, you know, campsite rules: do your best to leave your partners in a better state than you found them in.

You are not morally required to be in a marriage or have children. Dishonesty--hiding partners from each other, hiding an STD, pretending to want a long term relationship to get into someone's bed--those are the things that are actually morally repugnant.
posted by JDHarper at 10:51 AM on December 3, 2021 [62 favorites]

How about you spend time with people who you enjoy and who share your values?

I am a woman who has absolutely zero interest in raising a family and I'm really not interested in ever being married, either, but I think dating is fun. When I think of personality types that are just gonna dry me right up, some guy going out of his way to be the cleverest and most debonair free-with-his-money man in the room like I'm just his accessory is pretty high up there.

Just be honest about what you want and don't want with everyone you meet, and spend your time with people who make you feel good about yourself.

And p.s. work on having an interesting personality before you flaunt yourself as god's most adventurous and suave gift to all women. We can see right through it.
posted by phunniemee at 10:55 AM on December 3, 2021 [59 favorites]

Setting aside the squickiness of calling yourself a "playboy", live your life the way you want to live it. Date a lot! Have fun! Live life the way you want to live it.


I want to give them an experience they won't forget, I want them to at least in the moment feel like complete bliss and adoration before some of them venture down the path of a miserable marriage to someone else.

Don't set yourself up as the platonic ideal of...whatever that is, held up as "this is the life you could have, if only you were fun like me, but you want to get married and be boring, so...". In the same way that you want to live life the way you want to live it, so do women who ultimately want to marry and have a family. Don't think less of them because of it, in the same way I presume you don't want people to think less of you for living the way you wish to live.

there is a kind of code of ethics for Playboys that they should adhere to.

You really need to not think of it like this. If you want to just serially date women, that's fine. There's no club for it, there's no rule book, you don't need to brand it as anything; just treat the women you date well while you're dating them, and when it's time to end a relationship you're in, don't be an ass about it. That's pretty much it.
posted by pdb at 10:55 AM on December 3, 2021 [56 favorites]

I want them to at least in the moment feel like complete bliss and adoration before some of them venture down the path of a miserable marriage to someone else.

So you're looking for internet strangers' judgement on your approach: dating without "looking for anything serious."

Instead, I'll make you a deal: I won't call you names or come to uniformed conclusions about what emotional states your approach will lead to if you agree to stop doing the same for those us of who choose to pursue committed monogamous relationships.
posted by Mr.Know-it-some at 10:57 AM on December 3, 2021 [20 favorites]

Since you're clear with the women you date that you're not looking for a long-term relationship on a cohabitation/marriage/kids track, there's zero problem with not looking for those things. Many women aren't looking for those things either, and if you and such women have a good time together, then awesome. There's nothing unusual or unethical about that.

The only thing that gives me pause is that the actual term "playboy" is a weird term with a lot of connotations for what actually sounds just like...being a well-off man who can afford to be generous with his dates. That you think of it as some special personality type is what gives me a little pause and makes me wonder what other assumptions/connotations you may be bringing to these relationships. But we can't tell that based on what you've said here. Is there some sort of feedback you're hearing from your dating partners that makes you think you're being selfish or unethical? If so, pay attention to that, especially any recurring feedback coming from multiple people.

Otherwise, you're just a person who is interested in dating but not in marriage. Stick with people who tell you that's what they're after too, and go forth and have adventures.
posted by Stacey at 11:03 AM on December 3, 2021 [13 favorites]

On one hand, as long as you're honest and low-drama about all this, I—a twice divorced woman who's not interested in a life-long commitment—would think it fine (and probably prefer it to monogamy).

On the other hand, there are a bunch of "savior" and "god's gift to women" ideas in your post that would make me say "no thanks" to a proposal like yours. I didn't marry into a life of unhappiness without ever feeling adoration + bliss, and now I'm desperately seeking that with a "playboy" before I throw my life away again. That's an inaccurate and unflattering generalization of women. I've never lacked for enjoyment and adventure, because I'm fully capable of generating it for myself whether I'm in relationship or not. I can afford the things I want and don't need a man to spend money on me and buy me gifts. What kind of "security" do you offer? I don't know what that means in this context or why I would need it.
posted by cocoagirl at 11:07 AM on December 3, 2021 [59 favorites]

Seconding that this is just called dating. The issue I would see here is that your concept of your role in women's lives sounds a bit patronizing and, in addition, there's a standard here that you can't know you're meeting. People in a non-serious dating situation with you are unlikely to give you any honest account of whether you are providing them "bliss," let alone whether you are doing so before they trudge down the road to fated misery.
posted by kensington314 at 11:09 AM on December 3, 2021 [13 favorites]

You do you, but why do you have to think your girlfriends are going to be miserable with someone else? If you could provide a few months of fun for a woman who then went on to marry someone else and live a perfectly satisfied life, would you still be ok with your lifestyle? Or would you be mad that you're not "her best" and then want to pursue her to prove your dominance?

Answer honestly, and you'll know whether you're an actual Casanova or if you're doing this simply to protect your ego.
posted by kingdead at 11:20 AM on December 3, 2021 [15 favorites]

It’s worth getting some therapy to make sure that this is actually a choice you’re making rather than a justification of limits imposed on you by trauma. Even if you’re fortunate enough to be trauma free, therapy can equip you with excellent tools to communicate, which will benefit you in love and life.
posted by The Last Sockpuppet at 11:20 AM on December 3, 2021 [11 favorites]

Ethically, I think where I'm having trouble with your question is that it sounds like you've kind of decided in advance what these hypothetical women are going to want (money and lavish gifts) and it sounds like you're commodifying it.

If what you want is to feel like you have zero obligations to the other person as a person and that they accept exactly what you want to offer in exchange for their attention, I think you'd be better off in a straight up business relationship - and between consenting adults that's fine.

If what you want is someone (or a group of someones) who want the same model of relationship as you, then I think that also is a-ok and as responses here indicate, there are plenty of women who also want low-obligation, short-term relationships. And then from there you look for someone who wants to do what you do - that's dating.
posted by warriorqueen at 12:10 PM on December 3, 2021 [10 favorites]

Serial dating is fine! Non-monogamy is fine! What makes them fine: being upfront with women that you date that this is the model of dating you want to pursue. What's not fine: love bombing them with affection, gifts, and the illusion that you are courting them in some sort of old-fashioned way that might lead to marriage, kids. etc.

Also, not everyone is miserable in marriage, so you might be projecting that onto other people.

If women you date are looking for long term, and you know you don't want that, then you need to make extra sure you are communicating what you do and don't want. It sounds like you are still figuring out what you want. First, you have to be okay with yourself, and what you want. And then you need to be upfront about communicating it. It's not ethical to pursue women who want marriage and kids with the idea you're giving them one last hurrah before they descend into misery with someone else. Like, that doesn't make sense, and it sounds shitty.
posted by bluedaisy at 12:12 PM on December 3, 2021 [12 favorites]

“I want them to at least in the moment feel like complete bliss and adoration before some of them venture down the path of a miserable marriage to someone else.”

A Woman here, a lot of your dating premise is okay with me personally and there was a phase where I enjoyed these kinds of relationships but I wouldn’t describe it as “bliss or adoration” as much as just having a carefree blast with someone fun and attractive… and if they had been envisioning me in the future living in a miserable marriage, as opposed to being the perfect catch for some lucky man, just not them… I think it would have felt icky.

Maybe to give you some more food for thought- I miss my carefree days A LOT sometimes, but it’s not the dinners and travel etc. It’s the freedom and the time….and the relationships I valued the most I think of the men were just really great company at a time in my life where I was growing a lot… maybe I could describe it like being a fun class at college- fun and engaging and memorable, but not as important a part of my life as my family is now.
posted by pairofshades at 12:14 PM on December 3, 2021 [24 favorites]

As long as you are honest, kind, and respectful to your partners, do what makes you happy.
posted by The Underpants Monster at 12:42 PM on December 3, 2021 [6 favorites]

I'd totally dig some fun, carefree dating! But "In exchange of their company I provide them security, money, gifts, I basically want them to have one of the best times of their life." doesn't connect with the way I live my life. My happiness comes from inside of me- it can't really be made happy or content by security/money/gifts provided by someone else. Just enjoy dating and connecting with people!
posted by Mouse Army at 12:43 PM on December 3, 2021 [8 favorites]

There is nothing wrong with anything you've described here.

You might want to think about what you are missing out on by never having a romantic relationship that lasts longer than a short time, which might include...

The deep personal and spiritual growth that comes from spending years with someone who gets to know you, challenges you, pushes you to be better and learn and grow.

Someone to see you through hard times, show up in the hospital, give you a sponge bath when you can't get out of bed after illness or injury, etc. Grieve with you when your friends and family die.

Someone who has been a witness to your life, who will look back on all those amazing memories with you, "remember when we... [fabulous escapade]"

You can not get married or have children, and not be monogamous, and still be open to having lifelong romantic relationships with women that you are intimate with for years.
posted by amaire at 12:52 PM on December 3, 2021 [2 favorites]

Relationships, even short-lived, less emotionally intimate ones, need informed consent. Both people have to be reasonably aware of what they're saying yes to. As long as you are clear, consistent, and honest about the level and type of intimacy you're offering, it is fine to date however you want to date. There are plenty of people like you out there, both other "playboys," and people who want to spend time with them.

As far as a code of ethics goes, the paternalistic attitude you seemed to express--that you know better than women do about their futures (their future 'miserable marriages')--does not exactly scream respect. Your language implies that people who DO want marriages are chumps or less enlightened than you, and that's not fair. If you want the freedom to choose not to marry/have a family, others should be extended the same freedom. I also think it would be morally icky to target these types of relationships to women without the power to exercise real choice (offering to pay rent or basic life necessities for poor/young women in exchange for adventures or sex). Probably there is an argument to be made that that is a transaction women are free to agree to, but on first pass it seems problematic to me. I'm not saying you're doing this, but since you asked about a code of ethics I'm mentioning it.

FWIW I don't know if you were using the term playboy and talking about "playboy ethics" as a shorthand for the sake of this question, but presenting yourself in these terms may be a turnoff because it seems like you are being a character instead of being yourself. The reason you probably sense some judgment from others is that most people feel they need intimate relationships to help give their lives meaning, and you seem to be avoiding that intimacy, at least in the dating sphere. That is your decision to make, but it doesn't fit the dominant script, so there's a disconnect.
posted by kochenta at 1:06 PM on December 3, 2021 [12 favorites]

The exchange part is the weird part. Your blissed out ladies get money and gifts and personal security guards (oh yeah that part is weird too) What do you get? Is the unspoken part you get sex with women?

There's a lot of great ethical frameworks out there about living non-monogamy / polyamory but I don't think what you are describing here really fits it - but maybe check those out and see if anything resonates.
posted by RajahKing at 1:28 PM on December 3, 2021 [5 favorites]

There is definitely a dating subculture out there in which (generally very upper-stratosphere kind of attractive) women are looking for men to shower them with gifts and adventures and have a fun time that is exciting and probably not long-term.

If you are asking if it is okay to participate in that culture that is fine, but the notion that these women are actually going to experience unquestioned "bliss and adoration" before unintelligently tottering off into an unhappy marriage because they don't know any better... you will certainly be indulged in thinking whatever you want because you're running the wallet, but you will likely get your ass handed to you eventually if you really do not understand the field on which this game is played.

If your jollies come from finding naive women to do this to, or from thinking of women as just so much less smart than your enlightened above-marriage self, that's super gross.

Also understand that if you want to play this game in the major leagues, you need to have a lot of money. A lot a lot. If you want to play it at a lower level, you need to be absolutely sure that the women you're with actually understand the game. Because there's a lot of women who are flattered by attention and also don't understand that they're not going to be the Special One who changes you. There are lots of men who are fine pretending they don't notice this playing out because they said once that they weren't looking for a long-term thing and so have legally performed all necessary disclaimers so why are you crying, and a very special type who truly enjoys the sadism of destroying women this way.

Like, if you want to do this ethically you HAVE to know and acknowledge and proactively manage the fact that lots of women do not want this same thing that you want but have been systematically programmed since birth to settle for scraps and hope the situation improves*, and so will willingly start from just any amount of attention. The women you can ethically do this with should be actively looking for your type of man. They're not going to think it's love, if that's what you were wanting.

*And THIS is where the bad marriages come from, not that women are less intelligent than you.
posted by Lyn Never at 1:38 PM on December 3, 2021 [52 favorites]

The way I see it is that 50% of this women divorce anyways and many of them have lacked that enjoyment and adventure in their life.

This is pretty big generalization and, to my ear anyway, has a patronizing / contemptuous edge to it.

You're not wrong for rejecting marriage, kids, etc. - MeFi is a solid example that there are loads of women out there who feel the same. I'd suggest, though, that both you and any potential partners will probably have a better time together if you treat them as individuals w/their own unique needs, wants, pasts, and potential futures vs. transient embodiment of a bunch of stereotypes that A) probably won't hold up on close examination; B) are possibly an impediment to seeing and getting to experience what's interesting about them in the first place.
posted by ryanshepard at 2:17 PM on December 3, 2021 [14 favorites]

Lots of women can travel and buy themselves expensive jewelry and have nice dinners and pay for their own cars and nice apartments and etc etc-- they don't need it given to them. So there's that.

Other than that, as others have said, as long as you are open and respectful and truthful beginning to end I don't see anything wrong with it as a lifestyle. Find some like-minded women and knock yourself out.

What I do wonder why it's important to label yourself. There are so many men and women who just want to hook up and have fun and move on and don't want to be married -- but you seem like you find the label somehow reassuring, which makes me wonder if you're using that identification to avoid even the idea that you might want something more long term someday.

This is also true of just asking the question, "Is this a bad thing?" Other than the occasional bursts of underlying sexism, of course it's okay.

Why are *you* worried about it?
posted by A Terrible Llama at 2:36 PM on December 3, 2021 [5 favorites]

I'd totally dig some fun, carefree dating! But "In exchange of their company I provide them security, money, gifts, I basically want them to have one of the best times of their life." doesn't connect with the way I live my life. My happiness comes from inside of me- it can't really be made happy or content by security/money/gifts provided by someone else. Just enjoy dating and connecting with people!

This is a really important perspective.

Look, I've been in this kind of transactional relationship before and some of the language and sentiment you're using here feels very familiar to me. From your post, it sounds like you're telling yourself and your companions that all the gifts and dinners are in exchange for an evening of pleasant company. But I really don't think that's true, deep down. Deep down, the gifts and dinners are what you feel on some level is *necessary* to compensate for not offering the traditional expected path of romance, commitment, marriage. In a way, you're saying, you are a woman, and all women want commitment, so if you accept these gifts and pleasures, you accept that there's no expectation of commitment. What you're really creating is a barrier, not a benefit.

In my particular transactional relationship, my companion was a brilliant, exciting person with lots of stories to share. He was also an avowed bachelor. His insistence on paying for everything turned a temporary but mutually heartfelt connection into a smeary, transactional thing. It was him drawing a line in a broader stroke than he needed to, out of his own need to establish a boundary that he didn't realize had already been drawn and accepted.

So please rethink the gifts and why you offer them. For most women, companionship and a great personality and honesty/humanity are enough.

You seem to think that there's a clean binary here of being either a generous playboy or a married man, and I'd like you to rethink that, both for yourself and for the women you're seeing. A dear friend who travels a lot literally has a woman in every port, and for the most part he's been successful in being clear about what he wants in life, while also enjoying cheerful and open companionship with some truly wonderful women. It's possible. The overt transactional part doesn't need to exist when you give people what they really want.
posted by mochapickle at 2:51 PM on December 3, 2021 [30 favorites]

There's nothing in this post that really says what you're getting out of this kind of dating/romantic relationship. Do you just want NSA sex? Do you want to be adored for your sexual prowess? Do you want to be admired for your hefty wallet? Do you want someone who indulges and affirms your hedonism?

Because you could also just have adventures and experience bliss with...a friend.
posted by brookeb at 2:53 PM on December 3, 2021 [2 favorites]

Per Metafilter, as usual, everyone else has soooooo many insightful comments.

IMHO- you've used words which raised the hackles on my neck as far as the relationships you're looking for. "provide" "exchange" "security, money, gifts"

Perhaps those words are fine for various relationships. And adults should be able to be navigate these.

I *love* the comment about "campsite ethics" - try to make sure everyone, in mind and emotion, are better than they were before.

But gads - to me- currency isn't your currency, emotional investment - however temporary - is your currency. Phrasing it as transactional with regards to trips and trinkets strikes me as odd (unless y'all know that upfront).

Enjoy your time with those you date. My only suggestion is not to abandon anyone because you feel the transaction went south, and you want out for another.

Playboy? An appropriate term, but playboys take care of the way others feel. It's not a bad thing.

Just an off-the-cuff response from someone far far far away from such an interesting lifestyle.
Good luck!
posted by mrzz at 3:24 PM on December 3, 2021 [1 favorite]

Half of me feels like you're straight up groping for the term sugar baby. And that's fine, consenting adults negotiating and all that. It's a system that works out quite well for some people. But as others have pointed out there's definitely some wording and implied attitudes in your post that give me a reason for concern, no matter how positively I view a woman's right to enter in whatever kind of relationship she wants.

The other half of me thanks you're groping towards some sort of ethical non-monogamy, avoiding the relationship escalator, or other non-traditional dating structure. Which requires a lot of honesty and communication and understanding and compromise. Be fully honest with yourself, how upset would you be if you bed a lovely lady and find out she is going to visit another male partner in a day or two? Several male partners? Her husband?

There are definitely ways to get what you want as described in the post, but I think you deserve to do some deep digging and figure out how and why you really feel about a lot of things before attempting to do so.
posted by Jacen at 3:39 PM on December 3, 2021 [7 favorites]

So in short I definitely don't think you're an asshole for wanting any of these things, but there are absolutely methods and attitudes to pursue it an asshole-ish or even evil ways.
posted by Jacen at 3:41 PM on December 3, 2021 [2 favorites]

The behavior you describe sounds reasonable within the context of honest and consenting adults.

The *way* you’re describing it seems a bit arrogant and borderline misogynistic. If someone started talking to me about themselves an their relationships in this way, the conversation wouldn’t last long. But hey. I don’t really like talking to people about their marriages either.
posted by aspersioncast at 3:47 PM on December 3, 2021 [7 favorites]

Playboy vs. committed relationship for life
things I enjoy vs. what is expected of me in society
in a committed marriage (you) vs. broke up after a year (her)
lavish lifestyle, full of adventures and memorable moments (your lifestyle as a man) vs. lacking enjoyment and adventure in their life (most women)
security, money, gifts (transactional exchange) vs. best time of your life (experiences, company)
complete bliss and adoration (with you) vs. miserable marriage (with their eventual partner)
work hard, giving back to my community vs. being in a marriage raising a family.

I'm noticing some thinking in extremes here, which may be carving out a very challenging and narrow line for you to walk. It's also creating unnecessary separation and distance. You may think you need that distance to set noncomittal expectations, but you don't. It's just a form of defensiveness. And besides, the distance and black-and-white thinking is going to make it harder to create mindblowing adventures.

This is because in order to give people these amazing moments of bliss, you kinda need to connect with them and be fully present in the moment. You have to love them in some way. The difference is what you make that love mean. Do you give it freely and without expectations or further commitment? By all means, give it! But don't fool yourself into thinking that your gifts and acts of service are simply transactional and emotionless on your part.

The type of relationship you ultimately want is possible. I will add that it does necessitate a higher degree of communication though, so that you don't mislead or hurt people, including yourself. Many will mistake your freely given love, your intense connectedness, your gifts, your kind words, your acts of service as committed love. That is how we're socialised, it's what many of us desire. But not everyone. Find the people who get you and understand what you're offering. And always be clear and kind with everyone.
posted by iamkimiam at 3:52 PM on December 3, 2021 [9 favorites]

If you're being straightforward and upfront, communicating clearly and freely, informing all partners that relationships are not exclusive, testing for STIs regularly, and assuring that your sexual partners are expressing ongoing positive consent, you're behaving ethically.

I'd encourage you to think about empathy, and to try to appreciate how an empathetic worldview might change (or not change!) your behavior.
posted by mr_roboto at 4:23 PM on December 3, 2021

I was looking at some of your earlier questions and I can't help reading this in the context of coming from a conservative, religious family and maybe a cultural background where at your age you should be marrying and setting up a household. That's a strong deep conditioning that sounds like it's weighing on you.

We, strangers on the internet, can't really do more than advise you to try and do right by your partners. That's as far as my moral judgement wants to go. For yourself, you might get some perspective by seeking out other people from your background who have also left and adopted a different set of values. Are you just looking for ways to make peace with your decision to break with your family's tradition? That might be a better line of investigation.

Try to do right by your partners though.
posted by i_am_joe's_spleen at 5:00 PM on December 3, 2021 [9 favorites]

I've been thinking about this question a lot, and I agree that you're fine if the women know exactly what they're getting into. However, your statement that you're offering "security" makes me wonder about that. Security in this context usually means marriage. If you're having flings, which is what this sounds like, I can't figure out why you think you're offering them security. So that makes me wonder how clear you are in your own mind about what is happening here.

I think the reason I've thought about this question so much is I'm trying to figure out why my reaction is that this just sounds very icky. And I think it's because the women don't seem quite like adult humans - not when you feel that you're giving them something wonderful by providing trinkets and toys. But I can also believe there are women who like getting the trinkets and toys and feeling spoiled by a man.

Be aware though that some women will be in this for what you spend on them. I don't believe that you're just trying to give them pleasure out of the goodness of your heart. It sounds to me like you enjoy being the guy who can spoil women and spend money on them and impress them with your wonderful personality traits. So be aware that some women who go for this are going to be using you for what you spend on them and offering a pretense of being impressed with you for who you are. I mean, the idea that these women will all end up in sad marriages remembering how wonderful you are - that makes me think that you're asking for some kind of emotional validation that women who want money might be very good at offering to your face while talking shit about you behind your back. And that makes me sad for you. But when relationships are as transactional as this sounds, people on both sides can be calculating. And I don't know what's really going on in the Trump marriage, but the transactional quality of what you describe sure sounds like Donald and Melania to me. That's probably part of where my ick reaction comes from.

It's good that you're even questioning this and thinking about it. I hope you keep thinking about it and have a different idea of relationships in ten years - you don't have to get married to have relationships with women where you're both just equal human beings who like to do nice things for each other.
posted by FencingGal at 5:20 PM on December 3, 2021 [14 favorites]

Also, try googling "sugar daddy stories" to get some ideas about how women in these relationships might be thinking of you.
posted by FencingGal at 5:21 PM on December 3, 2021 [3 favorites]

Reading your question from this summer about your divorce, I’ve gotta say: I don’t know the details of your finances, but I suspect that you’d be a bit surprised by just how much money/power it takes to convincingly pull off the sort of lifestyle you’re talking about. A lot of the playboy fantasy is about being independently wealthy and allowing that wealth to override social conventions; Bruce-Wayne-on-a-budget is going to come across very differently.
posted by a box and a stick and a string and a bear at 5:38 PM on December 3, 2021 [5 favorites]

You don't need money to do this. The experience you're describing does not hinge on money - it makes some aspects easier, sure, but your approach is what makes the experience.

My partner is something of a broke version of what you describe. When we go out together or stay home, we are almost always focused on each other and having a good time together. Be it a shitty dive bar and punk bands, or fancy cheese plates and cocktails. What makes it good is play - we connect at the level that this is what we want. Yes we are romantic, and love each other, and do domestic stuff too, but when he is with me (or his other partners) doing dating things he is all in. Which also means emotional vulnerability. Your entire post shies away from that, which will necessarily make it feel more transactional, less meaningful. Which may not have the result you want.

(I'm a 40 year old co-parenting with my ex, after a fifteen year relationship ended in divorce - I love my fancy times, but I'm not gonna trade my values for that, which includes "do not want marriage or cohabitation again" and "my career is important" and "I want to do things I enjoy")
posted by geek anachronism at 6:36 PM on December 3, 2021 [2 favorites]

Based on your previous questions I would suggest not framing this as some kind of permanent decision. You were married. You want to date casually now. Great! Completely assuming here but it seems like you were previously very focused on relationship with the outcome of marriage and the obligations you had. Now you're skeptical of that idea and you want to swing to the opposite extreme. As others have pointed out, neither of those are wrong. But it doesn't need to be a permanent swing. And you don't need to swing all the way to the other extreme.

Why not date casually? Have fun. Find yourself. Explore what you like. Don't have an end goal in mind and be open to what happens. Just make sure to be respectful and kind to everyone you meet along the way. I say this based on your previous questions where you always have a clear goal in mind that you think you need to aim for. It's okay to not know what you want and see what is feeling good. But make sure that it's actually making you feel good and not just superficially filling the void.
posted by aaabbbccc at 10:53 PM on December 3, 2021 [8 favorites]

I would be concerned that you might be love-bombing your partners or potential partners. If you are producing a whirlwind of romance and appreciation and magnifying how, if they go for a date with you they are dating up, but acting like you find the irresistible, you aren't giving them a chance to figure out if they actually want to date you or not, by being too sweet to say no to. You could be hooking them through greed, meeting needs for affection and appreciation that have long been unmet, or simply being so good that saying no feels like ingratitude at best, and like stomping a puppy at worst.

But this is not necessarily an experience that people want. If there is any chance afterwards they are going to feel worse than before they started you're not doing them any favours. Affection and appreciation that isn't consistent isn't real. If you date someone who paints and go into raptures over their art and discuss it with them at length, and tell your friends to buy their paintings and encourage them to shoot for a gallery show at Gallery Le Snob and even have a private word with the person you know peripherally who might get them the show, and then you don't continue to follow their art and and their career you were faking it. It doesn't matter if you told them only one or two dates, or not going steady, you faked the appreciation. It doesn't matter if you don't get them to sleep with them and the date is just a restaurant-art gallery-moonlight stroll holding hands and no kiss, you are still faking the appreciation.

If what you are doing is something like that, they you probably can get somewhere by asking yourself why you are doing it. One reason might be that you don't think you can get any dates unless you love bomb them, or pay for it. Another reason might be that you are fawning, that an upset or unhappy partner is so distressing for you that you are determined that Nothing Must Go Wrong and preempting any kind of criticism that might be leveled at you by them.

The fact that you asked this question indicates that you are uncomfortable about what you are doing, either because on some level you feel that you are paying too much for a date and are being used, or because you are concerned that you are using the women you date, by giving mixed messages.

You might be using the gifts and attention thing simply so that you feel in control. Having the power to create the perfect night out - and the power to withhold it - keeps you in a situation where you're not the supplicant hoping to find someone decent to hang out with and the one hoping to have a good time. If your partner stops the date before the waiter brings the bill, taking the gallant role of "Of course I will take you home! Let me get your coat!" and doesn't leave any room for, "well damn, I was hoping you'd like the private jazz club I was going to take you to, and now what the hell do I do with the silver charm bracelet..." Instead there is the assumed role of the gallant, unflappable, untouchable James Bond for whom a date with cold feet is no more distressing than a sniper shooting her as you exit the hotel.

Lots of people have said that serial dating is fine, and not wanting to get involved permanently is fine, and being a bit of a slut is fine - I personally advocate six weeks between sexual partners because it seriously cuts down on transmission of HIV and gives everyone involved a chance to figure out if they really want to do it - but if you want to have lots of sexual partners and there is no fraud or coercion about it and the sex is good and you think your partners are wonderful and they think you are wonderful, you're providing a net good to the world. There is nothing wrong with having lots of partners and loving and admiring them and leaving them feeling loved and admired.

But you may still be carrying a wounded ego, and protecting yourself from harm in ways that could turn into a habit and block healing. If you are, then you are also probably sometimes causing your partners to feel bad. If you dial back your ego, you can see what hurts you, and not be in denial about the true feelings others are experiencing, but you also leave yourself open to hurt. None of it is easy. We evolved into an intelligent species and developed complex language all so that we could negotiate personal relationships and try to figure this out.

I think a good place to start is by looking at the details on your dates, and figuring out which parts don't feel good to you. You might figure out if you feel uncomfortable at the parts where your date takes away some of your control, or if they are the parts where she fails to show appreciation, or if it's the part where you worry that the gift might not be enough, or the part where you feel resentful that you have to buy the gifts and that her appreciation is just a role she is playing.

Always be kind. To others, but also to yourself. You're on the right track.
posted by Jane the Brown at 8:42 AM on December 4, 2021 [9 favorites]

It seems like insecurity to me- if you want to have casual relationships, that's fine, but why does it have to be an exchange of your money for her time/sex/etc? Why wouldn't someone want to be with you for the pleasure of your company? I noticed that you mentioned in one of your last questions that you actually had very little money, and perhaps things have changed, but you don't need to treat someone lavishly for her to have a good time. For me, spending time outside in a park or having someone cook me a meal at home is luxurious. If you want to do things that cost much more, that's your choice, but you don't need to do that to impress someone. And yes, there are women out there who don't want long-term relationships and are also perfectly able to take care of themselves.
posted by pinochiette at 10:30 AM on December 4, 2021 [5 favorites]

Also, try googling "sugar daddy stories" to get some ideas about how women in these relationships might be thinking of you.

Was there anything in particular you were referencing here? I googled exactly that and it's basically bringing up stuff that I guess would be arguing for some dudes to become sugar babies and when I encountered perspectives supposedly from sugar babies themselves I get the distinct impression it was written with one hand by not the sugarbaby. That and straight up erotic fiction.
posted by GoblinHoney at 11:13 AM on December 4, 2021 [1 favorite]

Also, try googling "sugar daddy stories" to get some ideas about how women in these relationships might be thinking of you.

Was there anything in particular you were referencing here

I'm sorry, and thank you for bringing this up. I posted too quickly - I was vaguely remembering a Buzzfeed article that had some sugar babies who were very upfront about how this was a transactional relationship.

Better, perhaps, is this New York Times article about the website Seeking Arrangements, which matches potential sugar babies and sugar daddies. I thought it was very clear that the women are motivated by the money. And the part I thought I remembered was that a man had said he hoped the woman loved him, and I remembered thinking, "Of course she doesn't - she met you on a sugar baby website." But that's not in this article, so I don't know where I read it.

What I'd really like to see is how sugar babies think of this when they've aged out as toys for men and are remembering it twenty years later.

Lesson for me: read more carefully before posting links or recommending searches.

My general point for the OP was that the women who are appreciative of this outlook on dating are very likely not all that interested in him as a human being and might be just using him for whatever they can get.
posted by FencingGal at 12:21 PM on December 4, 2021 [1 favorite]

This is not a constructive answer per se but it is reality check to you. Having looked at your previous questions and this one, my visceral response is "Ewww". I would suggest doing a blunt self-evaluation and, if possible, having a knowledgeable 3rd-party perform one too - especially one who has read these questions. There's a lot of uncomfortable aspects all-in-all with respect to your attitudes towards women and relationships in them that are - very bluntly - not positive or respectful. And they're there - you wrote them - in black-on-green that you should be seeing
posted by DeepSeaHaggis at 12:21 PM on December 4, 2021 [13 favorites]

As I read your question, I am reminded that people are motivated to do things that make them feel good about themselves, and will go to great lengths to avoid doing things that make them feel bad about themselves.

What is it in your relationship plan that makes you feel good about yourself? I might guess that you imagine that you will always and ever be appreciated for the magical experiences you bestow on your dates, both in the moment and in their cherished memories. Is that the motivator? Why does that make you feel good about yourself?

What is it that you’re avoiding in this relationship plan? Never having to deal with day to day realities? Never facing disapproval? Never having to have hard conversations? Never getting bored? What is it about those things that make you feel bad about yourself? What’s unbearable?

This is where doing the hard work of counseling will help you. The shame that’s driving this is almost certainly affecting other relationships in your life—family, friends, professional relationships.
posted by Sublimity at 5:02 PM on December 4, 2021 [6 favorites]

If you want to be a sugar daddy and everyone's in the know and consenting, fine. The one thing I might be concerned about is if you shower them with too much money/gifts/attention/whatever, some folks might actually get attached to you and you don't want them to be. Maybe just stick to the actual sugar daddy websites to look for dates?
posted by jenfullmoon at 6:51 PM on December 4, 2021

You sound like someone who is getting put down from outside somewhere. Nothing about what you said seems concerning to me as long as everyone is up front. Live your life man, you sound like you have a good one. If that rings hollow, maybe therapy can help you find out why you can’t just push the gas and move on.
posted by Geckwoistmeinauto at 9:31 AM on December 5, 2021

It's really interesting that you wrote up a whole post about dating and relationships without ever mentioning what YOU want or need or desire. Instead you wrote the whole post from (what you imagine is) the perspective of the women you will be sleeping with. You don't even directly exist in this post except as someone seen through the eyes of those women: how they will perceive you, what they will get from you, how they will feel when they're with you, how they will remember you after you're gone from their lives.

It's like the women are the only ones who seem real and alive in it.
  • they're the ones whose lives have a backstory: they've been in terrible, boring marriages, and now they're divorced and finally ready to have fun - you, on the other hand, have no backstory, you've simply appeared out of thin air into their life,
  • they're the ones who have any feelings or motivations: they're seeking adventure and they love to be pampered - you, on the other hand, have no desires or motivations of your own and you just exist to fulfill theirs,
  • when you and this woman are dating *she* is the one who is experiencing bliss and fulfillment - meanwhile you might as well be absent from the scene or swapped out for some other anonymous guy for you're reacting to it,
  • when you and these woman part ways, *she* is the one who experiences the encounter as a beautiful memory - how you will feel about it is a total mystery,
  • and ultimately *she* is the one who continues to exist into the future and move forward with her life (by getting into another miserable boring marriage), while you are kind of stuck in an endless time loop, repeating the same story with different women each time like Groundhog Day, with ability to imagine a future or a way to progress for yourself.
Because of this extreme lack of any information about your own motivations and needs in this post, I felt compelled to read between the lines.

Reading between the lines it seems to me that your core need when you seek romantic/sexual partners is that you desire to be seen by your romantic/sexual partners, because your fantasies are all about how you wish to appear through your partners' eyes.

IDK if this is accurate? But something to think about... And definitely, even if this is not accurate, please take the time to write down for your own benefit what YOUR needs and desires are when you look for partners. Articulating your needs gives you valuable information about what to ask for, who you're compatible with, how to assess the compatibility of your partner, etc.

Like, let's say that my reading between the lines is correct, and that your core need is the desire to be seen by your partner. This is useful to know! Other people may want love, children, commitment, partnership, sex, acceptance, validation, rescue, etc. but you want, specifically, to be seen. Knowing this means you can say directly to your partner, "I make an effort to be a playful, sexy, mysterious, generous boyfriend," which communicates to them exactly how you wish to be seen. You'll probably find it very affirming to be with partners who explicitly notice these qualities in you out loud, as opposed to partners who don't make any observations about you.

Whatever you manage to articulate about your needs will similarly help you identify how to succeed at relationships.
posted by MiraK at 11:59 AM on December 6, 2021 [8 favorites]

I agree with a lot of what folks have said above, including that you may want to explore why you've decided not to ever be open to the possibility of falling in love again. But one more thing concerns me that I haven't seen mentioned. Everyone has talked a lot about being honest and up front with the women you're dating about the fact that you don't want a commitment or any real emotional connection. However, you say:
I want them to at least in the moment feel like complete bliss and adoration...

People don't only communicate in words. So no matter how many times you say you're not looking for an emotional connection, if you also communicate them that you adore them, either verbally or nonverbally, that's going to be very confusing. If you act like you're in love with someone, shower them with compliments and gifts, make them feel that bliss you talk about, some of them are going to fall for you. And that's not their fault, because even if you told them you weren't looking for something serious, it's not unreasonable for them to be upset and disappointed and even heartbroken when a man who conveyed to them that they adored them then tells them they were just one in a series of adventures for him, and cuts things off when she thinks things are going well and she's falling in love.

So if you want an activity partner (for activities including sex, but also travel and adventures and all the other things you talk about), say that. But also act like it. Don't communicate to a woman that you adore her if in fact she's just a temporary sidekick who won't be around for very long.
posted by decathecting at 4:56 PM on December 6, 2021 [2 favorites]

Your post is all red flags. If you are really honest, it's not unethical, but I think you are seeking a form of masculinity that is a mirage, and that does not lead to a healthy state of being or to happiness. Yes, there are women who are attracted to displays of wealth and someone who pays for dates, drives a nice car, whatever. I know women like that, and after the initial attraction, they really want someone interesting, interested, authentic, fun, real. For me, the non-negotiables are kindness, intelligence, honesty, with sense of humor a big bonus. The guys that have all that are terrific guys.
posted by theora55 at 3:38 PM on December 8, 2021 [2 favorites]

I think I have a fair idea of what kind of life you're imagining. First of all, while this recent marriage is breaking up, I notice you've also had (AskMe'd about) at least two other engagements in the past 8+ years, so I'd put some thought into how you are connecting with your partners and what your intentions were/are, y'know, existentially.

I'm a bit older than you and (attempt to) do quite a bit of online dating due to social anxiety issues in the first half-plus of my adult life, and you should know that your options change as you get older. There are a significant number of women who appear to always be on vacation, have pictures in locales all over the world, are conventionally attractive, and do not appear to have a career. At the same time, there are single women who have careers and like traveling internationally twice a year who might also appeal to you but wouldn't need or put up with the gifty caretaker trope. Serial monogamy can take many forms, and if you're anything like I was, my advice is simply to stop trying to get married for awhile.

One of the few things I believe as an article of faith is that everybody can have the life they imagine they want, but given the last third of your life you might mull whether your current initiative will result in another question here. Not that there's anything wrong with that.
posted by rhizome at 11:33 AM on December 29, 2021 [1 favorite]

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