Seriously dating a single mom: yes or no

Gaturro

Tool-Bearing Hominid
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Oct 25, 2021
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My best friend is 24 years old. He's seriously dating a 30 year old woman (they met less than 2 months ago).

The woman has two children, and their father is dead.

I'm trying to tell my friend it's a bad idea, because I care about him, but he's telling me it's too late because he likes her.

Could you provide me with some arguments to convince my friend not to date her?

Of course, this will be ultimately his choice, but I would like to hear your thoughts - and if you disagree with me, I would like to hear you as well.

By the way, my friend isn't a PUA and doesn't know anything about this community. Obviously.
 

topcat

Modern Human
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Dec 20, 2012
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715
My best friend is 24 years old. He's seriously dating a 30 year old woman (they met less than 2 months ago).

The woman has two children, and their father is dead.

I'm trying to tell my friend it's a bad idea, because I care about him, but he's telling me it's too late because he likes her.

Could you provide me with some arguments to convince my friend not to date her?

Of course, this will be ultimately his choice, but I would like to hear your thoughts - and if you disagree with me, I would like to hear you as well.

By the way, my friend isn't a PUA and doesn't know anything about this community. Obviously.
I’d leave him to it, there’s nary much you’ll be able to do to dissuade him.

As a good friend, your best bet is to keep an eye on him and provide logical council when he goes to make more foolhardy decisions..
 

Troy

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Anyone on here can remember when you were a child (or you know of a child) and your (their) parents said "don't touch the fire or the pot on the stove".

And you or the child STILL disobeyed and still touched the fire. This is what will happen if you say anything to your friend.

Let him have a good time. Let him get in her sweet watery guts and have a good time. Yeah yeah. It is only a matter of time before he gets burned. And he will know better through experience.

How do I know? I made the same mistake myself dating a single mom. She had a 4 year old son and repeatedly flaked on our date nights. She always had something going on:

"my son lost his school shoes and is stuck in the principals office"
"i have to cook dinner and my son is making a lot of trouble in the house"

blah blah. Eventually I got tired of it and I cut it off.

What I do recommend you do is still be a good friend. Let him bring situations to you. Trust me, its a matter of time before he brings more issues to you. And when he does, give him the guidance he needs so he makes smarter decisions.
 

Chase

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Oct 9, 2012
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@Gaturro,

I've advised a variety of guys on girls I knew were bad news for them.

In my experience you're at a disadvantage trying to dissuade him as a friend. I've had some guys take my advice and cut things off with women whom I was advising on the forum or as coaching clients, but friends? Never! They plunge headlong into those doomed relationships.

Like @topcat and @Troy note, he is probably just going to have to experience it himself.

One difference I would say... with a few friends I've really tried hard to "save" them and it didn't work. I don't do that anymore. Nowadays if I see a guy wading into a toxic relationship, I will point out to him, in as neutral a manner as possible, the various signs I see and what his likely outcome will be, then tell him ultimately it is up to him (because it is). That seems to work better -- then the guy doesn't feel like you are trying to drag him away, only that you have given him some counsel, which he can mull over or dismiss at his leisure.

All that said... if this friend isn't good with women, it's not necessarily the case he is going for a bad deal here.

It's not like this is a woman who divorced her husband and put him on alimony. Or whose husband left her because of XYZ flaws she has.

The husband died. Life happened. That sucks.

Could well be she's a fine woman who is better than this friend could normally get, but she's trading at a discount due to the baggage of two kids.

No guy with choice should take a gal with kids, unless he doesn't want any himself and he wants to be able to date a woman without her catching baby rabies and trying to get him to impregnate her (or trying to trap him with a pregnancy).

But if a guy doesn't have much choice, sometimes taking the kids along with the chick allows him to get a more top shelf gal who'd normally be unavailable to him.

Don't assume that just because he's your friend he "deserves better." I used to think that way about friends... later on I realized "you know what, there's a REASON these guys ended up with these girls!"

Chase
 

Vision

Tribal Elder
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Have you heard about women getting into abusive relationships and staying in them because he loved a guy?

I can't tell you how many times I've talked to women who were like, "this man is a narcissist and abusive and horrible and..." and when I ask why they're seeing the guy, they say that they are in love or attracted or whatever.

Yeah, well, guys are the same way... people say men are "logical" but we're actually driven by our emotions too... we get into bad situations even though we know they're bad (my brother goes from one abusive relationship to the next, even though I warn him each time)... we buy stupid shit because we want to feel good about ourselves and impress women (totally emotional)... we are driven by our emotions.

If he's "feeling it" with her, he's got to feel enough pain associated to getting into situation that it outweighs the pleasure he's experiencing by getting into it.

If he doesn't feel that, he'll get into it... and he'll do it over and over and over again until the pain overrides it.
 

DoWhatWorks

Tribal Elder
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I’d leave him to it,

Replying to this publicly that if I ever tried to act this way I would want offline & online friends to give me tough love and put me in line lol.

Just know if you tried to wifey some of your preferences, I would host a group intervention ;)

By the way, my friend isn't a PUA and doesn't know anything about this community. Obviously.

Have friends like this. Ironically my friends with game would listen to my well intentioned advice but my friends without game (who would benefit from it most) tend to ignore me and do their own thing anyway.

I've got a friend who's been texting a girl from Instagram for 1 year and a half and genuinely believes she'll meet up with him...

Spoiler Alert: She obviously won't - but he has to learn that for himself.
 

Karea Ricardus D.

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Oct 9, 2012
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626
You know, of all the girl-friends I ever had, the best one was a single mom. It comes down to what Chase said though: many single moms are in that situation because they're fuck-ups. Some ended up in the situation through no fault of their own.

That was the case of this ex of mine, the father of her child left her for another woman while she was pregnant (rough!)... you could say it's still her fault for selecting the wrong guy... but "he that is without crazy exes among you, let him cast the first stone at her."

The downsides of dating a single mom are obvious... most of those didn't apply in my case because her kids lived with their grand-mother in another city.

The upside is that single moms are very CHILL. They will create much less drama because their genetic purpose has been fulfilled already. This was BY FAR the most drama free relationship I ever had, and I didn't even have to deal with the kids ever.

So - I would say dating a single mom is only going to get you hurt IF the woman got into that situation through her own fault rather than through the fault of the father OR force majeure (death of the father etc.).

All that said - I still wouldn't recommend it in most cases (my specific setup where the kids were never around is very rare I suppose), you'd probably want to raise your own kids rather than someone else's at some point.

I wouldn't want to deal with another man's kids and I only dated her because I didn't have to do that. That would have been a deal breaker for me, personally. But for a man with less options I can see how it still might be appealing if it's that or nothing.

So not all single moms are bad news... it depends. In my case the girl was the sweetest and most drama free chick I ever dated. Ex model too and had a lot going on upstairs. High paying job, business degree, we usually watched Dragons Den and Shark Tank together instead of the usual chick crap.

So I would say it depends

- what's the situation with the ex
- what's the situation with the kids
- what does he want out of the relationship
- what are this guy's other options
 
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