Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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someone sounds intrigued.

chiken said:

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The never married at 44 would make me pause but not exclude dating him. The partying like he's 22 would concern me but if he is responsible with finances and a general adult, it wouldnt be a deal breaker.

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this is the messed up logic of woman....marriage in the west has not benefits for the man, this dude is smart.

Again, I wouldnt consider it a red flag, but I would wonder why.

Why i was trying to convey is that just because someone acts a certain way (parties a lot) doesnt mean theyre not responsible. It CAN mean that, but not always. If someone had their life together and chooses to enjoy their downtime by partying, I have no problem with that.

I thought you were better than that. Shame.

Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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Long answer:

This may or may not be a red flag. It depends on what YOU'RE looking for.

If you want a meaningful relationship in which you will invest emotionally and move toward building a life together it is a big ****ing red flag. Move along. Don't even bother.

A man who at 44 has not sought to build any sort of meaningful romantic relationships does not want to. It is highly unlikely at 44 if he is still partying like he is 22 that his goals will change.

His history indicates very clearly that he values immediate gratification over building long term relationships. And if you begin dating him, that will not change.

That being said, if YOU are just looking for someone to party and have a casual relationship with that carries with it absolutely no other expectations regarding commitment or long term goals, then go out with him and let him show you a damn good time.

The point is- his previous history (or lack thereof) and current behavuor at 44 tells you exactly what he is looking for in someone to date EVEN IF HIS MOUTH SAYS SOMETHING DIFFERENT. Actions speak louder than words.

And even if he has changed (though his partying ways indicate he has not) at 44, with his entire life spent partying, it is highly unlikely he will have the skills with which he can successfully navigate and foster a long term relationship without ****ing up and screwing you over in the process.

The important thing is to go into it with eyes wide open, know what you want and know that based on his actions and lifestyle no matter what else he may tell you, what he wants and what he is capable of giving you is a casual thing.

Pirate, as someone that is divorced with kids, I couldn't seriously date someone that is single and never had kids since I have kids, however, you don't have kids, as I recall…so just go with the flow and see where it goes.

Sooper Jeenyus said:

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Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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Pro tip: no single man has lots of hot female "friends." Those are hot female acquaintances that he would bang if given the opportunity.

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Oh, look who just watched When Harry Met Sally.

Ags4DaWin said:

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Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

---

Long answer:

This may or may not be a red flag. It depends on what YOU'RE looking for.

If you want a meaningful relationship in which you will invest emotionally and move toward building a life together it is a big ****ing red flag. Move along. Don't even bother.

A man who at 44 has not sought to build any sort of meaningful romantic relationships does not want to. It is highly unlikely at 44 if he is still partying like he is 22 that his goals will change.

His history indicates very clearly that he values immediate gratification over building long term relationships. And if you begin dating him, that will not change.

That being said, if YOU are just looking for someone to party and have a casual relationship with that carries with it absolutely no other expectations regarding commitment or long term goals, then go out with him and let him show you a damn good time.

The point is- his previous history (or lack thereof) and current behavuor at 44 tells you exactly what he is looking for in someone to date EVEN IF HIS MOUTH SAYS SOMETHING DIFFERENT. Actions speak louder than words.

And even if he has changed (though his partying ways indicate he has not) at 44, with his entire life spent partying, it is highly unlikely he will have the skills with which he can successfully navigate and foster a long term relationship without ****ing up and screwing you over in the process.

The important thing is to go into it with eyes wide open, know what you want and know that based on his actions and lifestyle no matter what else he may tell you, what he wants and what he is capable of giving you is a casual thing.

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It's possible he was in a committed relationship or a couple of those in the past 20 years, maybe even engaged or living together, and maybe he had some woman rip his heart out and stomp on it over and over with a spiked heel to the point that he has chosen to remain carefree because he doesn't want to get that close again and end up with that same pain.

Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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44 and still partying like he's in his 20s is a red flag for me; the hot female friends doesn't bother me. Being divorced would not impact my sense on this.

Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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Dating him would likely mean one of your lives is about to drastically change.

He sounds like he likes to swim at the shallow end. Good luck!

Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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It's not the 44 and never married part I'd be wary of. Like others have mentioned, it's the partying like he's in his 20s

And that would translate to a whole lot of other baggage that would be a red flag.

As others have said it's the combination that is a red flag if you are looking for something serious.

Never married in your 40s just sounds smart to me at this point. But other red flags are there, in my opinion.

The partying isn't great, but I'd want to know more about the lots of attractive female friends. If he's hot and they're hot, why isn't he dating any of them? Do they know something you don't? Maybe he's an ******* or just has a ****ty personality? Or some of them are FWB? If so will he be honest about that and respect any boundaries you have in that regard?

I'll just say that my ex is hot and he has not met an attractive single (and a few who weren't single) woman in the last 5 years that he has not banged. And he is someone with some obvious red flags (being married for one). So I find it hard to believe that an attractive, single, emotionally stable, and trustworthy man could have a ton of comparable (and single) female friends and not one of them would want to date him or at least hook up with him. If you're actually interested in him that is what I would dig into, personally.

Is it Pitbull, Mr Worldwide?

Wait. Why is having been married a red flag?

Sorry, I meant that he was married at the time of a lot of the aforementioned banging. To me. A red flag to many women. But not all, evidently.

So a single, never married 44 year old with no children is supposed to sit at home every night?

aglaohfour said:

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Never married in your 40s just sounds smart to me at this point. But other red flags are there, in my opinion.

The partying isn't great, but I'd want to know more about the lots of attractive female friends. If he's hot and they're hot, why isn't he dating any of them? Do they know something you don't? Maybe he's an ******* or just has a ****ty personality? Or some of them are FWB? If so will he be honest about that and respect any boundaries you have in that regard?

I'll just say that my ex is hot and he has not met an attractive single (and a few who weren't single) woman in the last 5 years that he has not banged. And he is someone with some obvious red flags (being married for one). So I find it hard to believe that an attractive, single, emotionally stable, and trustworthy man could have a ton of comparable (and single) female friends and not one of them would want to date him or at least hook up with him. If you're actually interested in him that is what I would dig into, personally.

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Ag_N_Houston said:

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I would much rather date a man with hobbies, than a man that spends all his time drinking and partying.

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How are you going to meet him?
Door to door?

AggieArchitect04 said:

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TexasRebel said:

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Ag_N_Houston said:

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There is a huge middle ground between sitting home alone every night and partying like your 20s.

Most men that age have hobbies or friends/family that they spend time with. DIY projects, fishing, reading, working out, playing an instrument...

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How to stay single until 50 for dummies?

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You don't have hobbies?

I know lots of men (or even just people), single or not, that have hobbies. Doesn't even have to be anything spectacular and you don't have to be the best at it. Just be educated and somewhat experienced on it.

There's something to be said about walking in a room or sitting down at the table and being able to offer more than, "Bro, last night at the bar…"

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Which room is that?

Pirate04 said:

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Tell me if this is a red flag:
Guy is 44 and never married. He has a lot of single, very pretty female friends that he hangs out with and parties like he's still in his 20s.
Yes or no? Would it be more or less of a red flag if he was divorced??

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There's a saying. People should find other people that share their pastimes. Do you like partying like you are still in your 20s? If not, I'd pass.