[MicroBob]

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I've had numerous heart-to-hearts with friends about how I hate their significant other and think they're making a huge mistake.

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No idea how often you do this but you make it sound like you have done this quite a bit.

There's a difference between saying, "your S.O. is a jerk. Why are you with him?" vs. "Ummm, did you know that so-and-so is bragging to various people about banging your G.F.?"

The first one you are being judgemental about something that isn't as much your business in the first place unless there is a better reason for having the heart-to-heart beyond them just being rude. Some of those reasons would include the other guy sexing-up somebody else or slapping them around some or whatever.

But heart-to-hearts just because you kinda/sorta don't like the guy are dumb.

Good friend of mine started dating a girl older than him by 8 yrs or so and I still can't figure out what the hell he sees in her. Whatever. She's nice enough and he seems happy enough. Not my place to say, "Dude, you know you could do a ton better."
I have never said anything and, as far as he knows, I never had a problem with this girl.
There was no point in sitting him down to talk about it because it would just upset him and wouldn't accomplish anything good at all as you alluded to in your post.
Would be freaking rude of me to say anything since she wasn't really THAT bad.


Different situation:
My GF's best-friend likes me okay...way more than her ex whom this girl hated 100%.
But her best-friend still thinks my GF could do better than little old me and occasionally drops hints to that effect in casual conversation.
Really ticks my GF off. I just laugh about it because I can already tell she doesn't exactly think I'm Clark Gable.
GF wants to remain friends with this girl but doesn't think these occasional hints about how average I am are appropriate in the least.