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Old 11-25-2015, 04:01 PM   #81
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So maybe you are 39 and living in your parents basement.
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Old 11-25-2015, 04:01 PM   #82
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Maybe we could all donate and just get your a hooker? Save you a lot of headaches!
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Men aren't mature
... yeah, we can see that.


Honestly, given everything you've said, you just need to go for it.

At first blush, you may think asking for his permission is the gentlemanly thing to do, but she's her own person, not his property. If he's not okay with it, the friendship will already be strained by your merely suggesting it anyway. He cheated on her, he treated her like crap, he walked away. As far as I'm concerned, that makes the courtesy of asking him unnecessary.

Don't live with regrets of what could have been, especially if you really feel there's something special there.
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Old 11-25-2015, 04:05 PM   #83
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I have been on both sides of this equation, both times I wish I hadn't been after all the dust settled.

One permanently ruined a 10 year friendship that I wish I could mend, as he was 10X the person she was. And I was thinking with my wang. It was his ex, and I was the intruder.

The other was my ex, we were together 3 years, and it went down like 2 weeks after we split, and I found out he was running game on her before we broke up. It took 10 years before me and my friend could even be in the same room without wanting to kill each other, but we eventually patched it up. We had been friends since kindergarten, and this all went down in our mid-twenties. He regrets immensely doing what he did. I regret immensely the anger and things I said to him. But eventually we ran into each other in Home Depot of all places, caught up, and managed to bury the hatchet.

The one constant I typically see in these scenarios, is the relationship usually fizzles out, and you wish you had never chased after a piece of tainted tail. It's all great for a few weeks or month, when it has all the new sex, and new partner discovery, but once that part runs it's course, you just end up questioning how you could stab a friend in the back.

I know it is cliche, but I have 4 friends in my life, that are like brothers to me, and no matter what, we will be there for each other for life. No matter what. These are guys you would drop anything at 3 am to bail them out of jail, or pull them out of a ditch... whatever. Of all the women I have had in my life, there is only one, I would even pick up my phone for at that time of night, and it would likely be because I was assuming she wanted a piece of pylon.

You buddies will be there for you forever, even if you go a year or two without speaking. Women will not be.
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Old 11-25-2015, 04:08 PM   #84
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You buddies will be there for you forever, even if you go a year or two without speaking. Women will not be.
Disagree. The right buddies will be there for you forever, so will the right woman.
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Old 11-25-2015, 04:10 PM   #85
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Bro's before hoes
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Old 11-25-2015, 04:11 PM   #86
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Bro's before hoes
back to being 18
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Old 11-25-2015, 04:11 PM   #87
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Bro's before hoes
Such a teenager.
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Old 11-25-2015, 04:15 PM   #88
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Disagree. The right buddies will be there for you forever, so will the right woman.
From a male perspective I disagree. Probably because I have never have female friends I don't want more than friendship from. I'm not exactly good at the platonic relationship thing, and that is more my problem. But in most cases, I find your male buddies will be far more reliable than an ex. There is always the doubt there is the expectation of something more from either party or both I find. Even if they say they are just in it for the friendship.
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Old 11-25-2015, 04:17 PM   #89
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Such a teenager.
Buddies over bloodies?

(cause you know... periods.... You're bringing this out of me.)
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Old 11-25-2015, 04:20 PM   #90
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From a male perspective I disagree. Probably because I have never have female friends I don't want more than friendship from. I'm not exactly good at the platonic relationship thing, and that is more my problem. But in most cases, I find your male buddies will be far more reliable than an ex. There is always the doubt there is the expectation of something more from either party or both I find. Even if they say they are just in it for the friendship.
I'm also saying it from a male perspective, that's not the issue. You're also looking at it from a male perspective of a single guy in his 40s, that's the bigger view. The bond of a partner, a life partner is stronger than any friend will be.

If the OP thinks this woman is it, then go for it.
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Old 11-25-2015, 04:21 PM   #91
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(cause you know... periods.... You're bringing this out of me.)
I'm bringing your period out of you?

Don't know what to say, I'm flattered.
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Old 11-25-2015, 04:23 PM   #92
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Haven't read the whole thread yet but thought I should chime in because lots of posts have been negative. I dated my friend's ex and then married him. Her and I are still friends - though that may have been made easier by the fact that she moved to Ottawa and we don't see each other often.

Long story short - if you are both adults I don't think there is any issue. You can all be mature about the situation.
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Old 11-25-2015, 04:24 PM   #93
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Can man and woman become close friends without sex? If you think the answer is no then Pylon is right.
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Old 11-25-2015, 04:25 PM   #94
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I'm bringing your period out of you?

Don't know what to say, I'm flattered.
I'm relieved. I was about 11 years late.
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Old 11-25-2015, 04:27 PM   #95
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Can man and woman become close friends without sex? If you think the answer is no then Pylon is right.
There's a better chance of ending world conflict than finding the right answer to that question.
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Old 11-25-2015, 04:29 PM   #96
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Do you hang out with this friend on a weekly basis?

Would you call him one of your 5 best friends?

Are the ex-wife and him friendly with each other or is it awkward if they are in each others acquaintance?

Are you prepared to lose him as a friend to pursue this?

What would you regret more: losing this guy as a friend, or regretting that you never pursued what could have been a great relationship for you?

Those are the questions you need to ask yourself. As others have mentioned it is inviting trouble and a bit of risk into your life, but if you think she is worth it you also don't want to regret it for the rest of your life.

I have a friend who dated an ex of mine pretty quickly after we broke up. Wasn't overly long or serious though so not a direct comparison but it still sucked when it first happened. However now 5 years later they are engaged to be married, I am going to be in the bridal party, and couldn't be happier for them.

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Old 11-25-2015, 04:30 PM   #97
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I'm relieved. I was about 11 years late.
He knocked you up 11 years ago?
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Old 11-25-2015, 04:31 PM   #98
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LOL, go for it. If it works, perfect. If it doesn't, you can crawl back to your buddy and both of you can bitch about the same ex.
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Old 11-25-2015, 04:32 PM   #99
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He knocked you up 11 years ago?
I don't think you understand how sex works but if he knocked me up, I wouldn't be getting my period....

This is getting weird. I just wanted to rhyme.
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Old 11-25-2015, 04:34 PM   #100
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Bro's before hoes
But a bro should also be able to put his bro ahead of his own selfish jealousy.

If you are a good friend and can see that your buddy and your ex are a good fit for each other, then you should be able to put your own ego aside and let them give it a shot. It will likely still end the friendship, but it shouldn't be a situation where you have to instantly fight the guy.

Especially in the case where said bro has lost his own wife. It will put strain on a friendship, and could be awkward, but shouldn't be a "I'm so jealous, I need to punch you in the face situation at all."

Last edited by SuperMatt18; 11-25-2015 at 04:37 PM.
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