Is there something amiss with men who have been single for a very, very long time, or have they just figured out how to game the system while the rest of us toil in the consuming throes of love and heartbreak?

In general, there are two ways we tend to look at long-term bachelorhood. The first: It’s a 24/7 fuckfest lived out by ruggedly handsome playboys with vintage motorcycles, commitment issues and flowing, virile hair that bounces spectacularly as they flit from one adventure to the next, blissfully unencumbered by the burdens of love.

The second is that something must be seriously “wrong” with men who either choose to stay single or are relegated to solitude by circumstance. No one likes to be alone, the common sentiment goes, so anyone who’s managed to stay that way for years on end must either be a murderer or a hermetic incel unworthy of serious pursuit.

Neither extreme is accurate — obviously — but the mystique of the long-term single guy still remains. Is there something amiss with men who have been single for a very, very long time, or have they just figured out how to game the system while the rest of us toil in the consuming throes of love and heartbreak?

To find out, I spoke to five men whose wedding you probably won’t be attending anytime soon about the agony and ecstasy of perpetual singledom, how they ended up this way and what it’s really like to spend your life all by your lonesome.

‘I was accused many times of being an emotional automaton’

Hunter Berkman, 66: I didn’t choose to be a bachelor for life. It’s just that, despite my best efforts, I haven’t been with anyone for almost 30 years. So, I guess you could say the life chose me.

I was never really a ladies’ man (or a ladies’ anything, for that matter). I was handsome and successful when I was younger, and I had a few girlfriends here and there, but they were always just sort of “there.” I never felt “swept away” by my emotions, and I was accused many times of being an emotional automaton. I had feelings for them, but it seemed the volume was turned way down.

I’m not sure why I’m like this. My brother is, too. It’s weird. Especially because I have things a woman should want. I have a nice house, and a fair amount of money. I’m loyal. I’m a nice guy. Do they really need emotional intensity when they have all that? I guess they do, because here I am, talking to you about being a stag.

I wish I could say I was still looking for someone, but I’ve learned to live on my own. Not that anyone in my life seems okay with that. My mother is always asking me when I’m going to meet someone and settle down, and my nieces and aunts always want to know what the deal with Martha is.

Martha is an old friend of mine. Maybe my only friend, to be honest. I met her at work back in the 1990s (I’m in real estate). We always understood each other. She’s straightforward and simple, just like me. Beautiful, too. I couldn’t help but fall in love with her back then — perhaps more so than with anyone else — but she never returned the favor. She didn’t have to say anything, I could just tell. She was always distant. Charming, but unavailable. Cold, like me. She never dated anyone, either. She lived alone, didn’t have many friends and just kept to herself. The only way I can describe the way we cared about each other was that it was “formal.” It was a friendship by association; like we wrote our names next to each other on a piece of paper and were together in that way without the context to give it a feeling.

Sometimes, she came to family dinners. It was difficult having to remind everyone she wasn’t my girlfriend, and she got tired of them saying things like, “Hunter, you’re finally off the market!” So she stopped coming. I learned to close off the part of my heart that loved her. We both got different jobs, and we grew apart. I still see her once or twice a year, but the part of me that yearned for her — or anyone — has since shriveled up like what happens to fruit when you leave it out for too long.

Now when I think about having a companion or a sexual partner, I feel nothing. I saw escorts for a while, not because I was feeling sexual, but because I thought it might bring that feeling of connection back. It only made me feel more numb and alone though, so I stopped that, too. But I always appreciated their kindness. They were so generous. I’m grateful to them for that to this day.

I get around the boredom of being alone with routines. I get up early, trade stocks, walk on the beach, try to sell some houses and read the paper. I have steak or Italian for dinner, then I watch some football and go to bed. Same time every night. I see my mother every now and then. I see my cousins. I ask them what’s new. I stick around for as long as I can before the traffic gets bad, and then I leave.

When I get home, there are times I’m so lonely that it cripples me. Sometimes, I can barely move I feel so alone. But it’s gotten past the point where I’m not expecting anything to change. I feel bad, but I’ve long given up feeling bad about my life (if that makes sense). It’s a waste of time.

I don’t know if I’m happy. What’s happiness, anyway? I think I’d be happier if I didn’t have to work anymore. Then I could sit on the beach and watch the women walk by with a cold beer in my hand and just relax, waiting for one of them to catch my eye. Because even though I’ve been on my own for so long and I can’t imagine a future where I’m not, I still hold out hope that someone will come along and give me butterflies. I don’t want to die alone. I suppose few people do, but I’d at least like to think there’d be someone there who would miss me when I was gone.

‘I just don’t find the concept of lifelong commitments to be realistic’

Kelly March, 32: I’ve been single for 10 years now, by choice. People always ask me why. Don’t I get lonely? Don’t I want someone to share my life with? Do I just have unresolved commitment issues?

Much to their confusion, the answer is, No, I don’t. I just don’t find the concept of lifelong commitments to be realistic. People change with time, and greatly so. Who I was 10 years ago is very different from who I am today. If you need evidence of that, just take a look at the high divorce rate. Often times, the person you married — or are still dating — isn’t the one you fell in love with. And you’re probably not who they fell in love with, either.

Second, as a man who is lucky enough to have done well in my career, I’m of the firm belief that marriage brings with it a large financial risk. Marriage, if done at all, should be a healthy combination of the emotional and the logical; you can’t dismiss pragmatism. Most people do though. They let emotions cloud the reality of what marriage means for resources.

Third, I simply don’t think I’m suited for it. I wouldn’t consider myself unkind or uncaring, but I’ve chosen to focus on my career, and I’m a very self-driven person. I don’t think this works well in serious relationships; I recognize it’s asking a lot of a partner to often play second fiddle to my career, to not always be the priority and to expect her to largely handle her own life as I like to handle mine, by myself. Most women are, quite understandably, not up for a relationship like this; and two self-driven, motivated people that don’t really need each other isn’t most people’s idea of “romantic.” Besides, I’m fairly committed to remaining unmarried and not having a lifelong relationship.

On rare occasions when I do date, though, I never lie to my partners about what I’m looking for. I have a healthy sex life with friends with benefits (not random hookups), and find this type of relationship more rewarding. Friends are a good thing to have, and sex between two single people scratches the physical needs. I’m happy with my sex life, and get what I need. I also try to impugn on my partners’ freedom as little as possible. She can go out, have her hobbies I’m not a part of and do whatever she enjoys doing. I think few women tend to give the same freedom to their man, and have a greater need to feel loved, appreciated and not alone in things. That’s not a bad thing, it’s just different.

The most notable impact of being single for the long term is the massive amount of extra time you have. It isn’t the primary reason I stay single, but it makes everything else in life easier. It’s also, frankly, much less stressful to only have to deal with my own problems instead of a wife or girlfriend’s as well. I can work lots of overtime, stay in shape and have the time to still enjoy my hobbies. Single men can spend more time with their friends, whose company I largely find better. Honestly, my lifelong friends and I have more in common than I’ve had with any girlfriend.

This isn’t to say that there aren’t negatives; the love and support of a partner is never there to help you through hard times. You don’t have a safety net. But personally, I’m the type of guy who likes to keep issues private and deal with them by myself. For me, that means I love largely without romantic love, but I’m happy like this. I’m not a particularly emotional man.

There’s definitely a stigma about lifelong bachelorhood and some people certainly think it’s weird that I remain single. But this doesn’t bother me. Life is too short to live it for the approval of the peanut gallery, and besides, I’m not lonely at all. I have many other fulfilling relationships in my life with friends, family and even ex-partners that I find love and connection from.

If anything, I’m glad I know myself well enough to lead the type of lifestyle I know works for me. Not to mention, I’m happy this way. If I wasn’t, I’d make a change and live a different life. Some people just aren’t meant to be in marriages or lifelong relationships, and this isn’t necessarily a bad thing. “Whatever works,” as they say.

‘The women I see know that I’m not looking to settle down, which opens the door for them to pursue me more aggressively sexually’

Len Huxley, 39: Every morning for the past decade, I’ve woken up and made a conscious choice to be single. Even though I always have a few casual relationships going at a time (maybe three or four women every couple of weeks), I can’t — scratch that, I won’t — commit, and I plan to keep it that way.

Why? I get bored easily. I’d rather see three or four different women in a month than one woman four times, even if I like her. Once in a while, I’ll see a woman more than a few times as a way to sort of “test drive” a relationship, but it never works out. I still get bored. That, or they leave me to pursue something more long-lasting, which is fine by me because I usually have someone else to pivot to.

The women I see know that I’m not looking to settle down, which opens the door for them to pursue me more aggressively sexually. As a guy, that’s an amazing feeling: to be pursued rather than having to pursue them. The whole “thrill of the chase” stereotype is bullshit, I think. The only men who really seem to enjoy it are the ones who are so in-demand that picking up women has become mundane for them. Not for me. I find it wildly liberating to have a woman cut to the chase and go after me.

Not that it was always this way. When I was younger, between the ages of 13 and 30, I was enslaved to my heart. All I wanted was a committed relationship, but the women I knew weren’t having it. I got cheated on relentlessly, and I got hurt all the time.

Now that I’m older, the women I meet are looking for what I wanted back then: marriage or a long-term thing. But after going through all that, that’s not what I want anymore. Now I’m the one who wants to keep it casual. Funny how that works.

The best part of being a bachelor is how much freedom I have. I get off work at five on the weekdays, maybe have a drink with a lady or with friends, then have the weekends off to do whatever I want. Usually there’s a date, but the rest of the time, I’m wide open. I spend it doing solo endeavors (playing poker, going to a movie, shopping) or just having lazy time to myself, which I highly treasure. I love just laying around. It really recharges me.

It isn’t, though, a perfect model. It can get expensive. The unofficial rule is that I’m going to be paying for the dates I’m going on, and it really adds up, especially with multiple women. Plus, I’ll never be sharing rent or benefitting from dual income, which kinda sucks. There’s also the occasional schedule conflict (everyone wants to do something on Valentine’s Day, or holiday weekends), which means hurting feelings once in a while. Most importantly though, nobody is ever really “on your team”; you’re always on your own. Luckily, I rarely find myself wanting or needing that support. Even if I did, the trade-off wouldn’t be worth it.

The stigma I get for being single isn’t that bad, really. Women really get the raw end of the deal there. While I overhear the occasional remark like, “Single at 39? What’s wrong with him?” it’s not real pressure or judgement. A single, 39-year-old guy isn’t that strange or taboo. Plus, isn’t stigma a matter of personal interpretation? When someone asks you when you’re going to settle down and get married, it’s less them “pressuring” you and more them just looking out for your well-being. For them, marriage equals happiness, and they just want you to be happy. You can choose to take that personally or as a judgment if you want, but I don’t. I see it as a sign that people care about me, and I appreciate it.

‘I’m not super boyfriend material’

Nils Kovalevsky, 26: I know it’s weird to say you’re a lifelong bachelor when you’re only 26, but having been on my own for almost a decade after my last relationship with my high school girlfriend, I really identify with that term.

It’s hard to say whether I’m like this by choice or circumstance, but there are definitely some circumstantial factors that have made having a relationship impossible. For one, rent in New York City is disgusting, so I live at home with my parents. We live far, far outside the city, and I share a room with my brother. I work at a gelato shop down the street, which is fun, but it’s not exactly baller money. As a result, I’ve become sort reclusive. I can’t really keep up with the big personalities in the city, so it’s easier for me to just be myself out here where I’m more isolated.

All of those things just make it very clear to me that I’m not ready to give a partner what they need. I have respect for people’s time and effort when it comes to finding a potential partner, so I’m not pursuing anything with anyone right now. It would be irresponsible for me to do so — along with funky and awkward. I’m not super boyfriend material. Sure, that makes me a little lonely, but I don’t think I’m any lonelier than someone who’s unhappy in a relationship or someone who is surrounded by dates but doesn’t connect with any of them. There’s just a baseline loneliness that’s part of being a human, especially in New York, and it’s just not that uncomfortable for me.

I do have a lot of free time, but I wouldn’t necessarily say I’m using it to pursue my dreams or develop myself. I’m feeling kind of lazy right now and enjoying being able to feel that way. I use my time for hobbies like reading and gaming, which is nice, but I don’t think being a long-term bachelor always means you’re living your best life. It’s certainly not sexy or flashy. I’m proof that you can still be in limbo and not at your full potential when you’re a single guy. I’m a little mediocre at this stage in my life, but I’m confident enough to be okay with that and to know it might change in the future.

At the same time, I choose to live this life. I know that someday I’ll move out, be more financially independent and be in a different headspace than I’m in now. But for the time being, I’m still growing into the person I want to be. And until I get there, I’m fine being alone.

I do wish people would pressure me to date a little more, though. I can be pretty stand-offish, bitchy and closed off, and sometimes people are scared of me. So there have probably been some missed opportunities I would’ve taken had I felt a little more encouraged to do so. It might be then that the apathy and acceptance that my friends and family have toward my situation have contributed in a small way to where I’m at now.

‘It’s strange how alone you can feel when you’ve met every boy in the world’

Nathan Withers, 70: I’ll tell you this much: When you’re a young, good-looking buck with your whole life ahead of you, it’s pretty exciting to be a single guy with no ball and chain. I had many, many men. Enough men to fill an ocean. Even some women, too (but that was just the 1970s, darling). Maybe I’ll meet them all again some day in heaven, and they can remind me what their names were! They were all so gorgeous. Just sun-kissed, always young. I could never have just one. How could you, when this world is just bursting with beautiful men? I tried them all, and when I was done, I looked in the mirror, and suddenly, I was 60! Or 70! Or 100, or however old I am now! Maybe 351. I’ve lost count. Suddenly, all the men I used to run around with are dead, or too young to want me. It’s strange how alone you can feel when you’ve met every boy in the world.

I don’t know that I long for a partner, because I’ve never had one around long enough to know what that’s like. But I do long for a companion. I’d like someone to crush up my pills and put them in my yogurt for me when I get too feeble to take them by mouth. I have some surviving friends — the old farts — but I do wish I had a man, or a couple, in my life. I do have my little dog, though. I guess that bastard keeps me busy enough as it is.