Awkward

So, my best guy friend has this girlfriend who's kind of an infant. And she's nice, and he likes her, but sometimes he complains about their relationship. And this puts me in an awkward position. I want to be supportive and agree with him, but I can't cross the line and be like, "You are so right. That manufactured drama was a bunch of toddler bullshit. Tell her to put on her big girl panties and quit whining."

Because, well, yeah: he can talk shit about her being a giant baby, but if *I* say it, he'll have to defend her and be like, "don't talk shit about my girlfriend." And if he takes my advice and tells her to grow a pair, it probably won't go well, and then he'll be mad at me for giving him bad advice.

So I'm in this awkward position of trying to figure out what tone to take when he complains. I know my advice is probably terrible, because my love life has been a 25-year-long train wreck, but I'm much better at giving advice than doling out sympathy. I'm trying to get better at the sympathy bit, but I have a short attention span when it comes to whinging adults. I can say "there,there" to a child all day long, but an adult? Either quit whining or get a room and have a good cry, but leave me out of it.

This probably makes me kind of an asshole. Or, I dunno: a dude? Yeah, it makes me a *dude*, doesn't it? I'm just not wired for sympathetic maternal behavior towards grown people, and I have no idea how he can spend fifteen minutes having the same conversation over and over:

"My cat's been missing for ten minutes. What if he's dead?"
"He's just hiding somewhere in the house. He's fine."
"But what if he's dead?"
"He's not. He's hiding. He'll be fine."
"BUT WHAT IF HE'S DEAD?"

Lather, rinse, repeat for two separate fifteen minute phone calls.

My head would totally explode if I was on the receiving end of that phone call.

I don't have a point, really, I'm just trying to figure out what tone to take because it's happening more and more.