Thanks for that story - what a good phrase to remember Judy. I too have a friend that it may help me with.

Judy, it's hard to step away from "overfunctioning", isn't it? I think I'm more successful at that as a parent than as a friend.

BTW, Mr. April and I are having lunch today with Friend and Mr. Friend, so I will have a chance to practice all these important skills.

Overfunctioning, what a great word, April. Life does seem to take continual practice doesn't it?? Have an enjoyable lunch!

Lunch report: first, it was just us ladies, no husbands. Second, I did hold firm in my resolve to be only supportive without actually fibbing if asked for an opinion.

The part I am most proud of -- managing not to clutch my pearls at this:

April: Yes, that [off-the-shoulder dress, pictured on phone] is very pretty. Not sure how it works with a bra?

Friend: What bra?

OMG…<laughing so hard over here>

April, you are a kind and patient friend!

Aquamarine, I assume the friend was assuming a built-in bra, which many dresses that would otherwise be "awkward" have. But I guess that isn't funny.

Wow. Having read all of this - and been in a similar (albeit non-fashion-related) situation - I would take a big step back and assess the friendship, i.e., knowing her, what can I exactly say to her to cut through all the dissembling, without crushing her feelings?

And how do I handle this in a way that I don't feel resentful and annoyed that my time and attention are being pulled into this repetitive loop?

In this situation, I would say, "Look. You keep asking me for ideas, and what I think. But you keep going back to these particular styles, and then you aren't happy when you look at the photos. So let's look at the photos and figure out what you didn't like about your outfits, and what would have made them something you liked. And go from there."

And while I get that maybe she doesn't want to look like the matriarch-MOTG, and spend a bunch of money on a dress that she won't wear again... sometimes you gotta take one for the team, and satisfy the mob.

Hmm. If you approach it like she's playing a role in a soap opera, and 'let's find you the perfect costume for this program', I wonder if that might appeal to her? I sense there is already drama.

Maybe reference Lisa Vanderpump from Real Housewives of Orange County. She's a bit flashy, but she also has some elegant looks.

Maybe without getting into a full on "session" you could ask her who the most important person at this event is and assuming that she will not choose herself, how can she best serve the interests of that person.

I filtered every factor of my presence through my daughter's best interest at her wedding and felt like I was exactly who she wanted me to be and who I wanted to be for her and myself. It was a shining moment then and I am still pretty pleased with myself now, haha.

It's such a complicated time maybe she doesn't have to pressure herself to resolve everything with a statement at this event.

MB ftw!

Excellent advice Phoebe.