Ruthless Advice for Upper West Siders: All of the Answers With None of the Expertise

By Karen Bergreen and Cynthia Kaplan

Well, it’s been a year. Lots we could say about it. HOO BOY! But we won’t. For now we’ll just thank all you Upper West Siders out there for your wonderful questions and your mostly well-considered comments. There were some whoppers, sure, but the life of an Upper West Sider can inspire that. There is room for all of it at Ruthless Advice. Everyone is welcome and everyone will receive the same lack of expertise. One final note: Our love goes out to the friends, family, and fans of that honorary Upper West Side mensch, the director Rob Reiner, and of his wife, Michele, a photographer. Together they led a life of art and activism. And Rob Reiner wrote about our dear neighborhood and its denizens with humor and generosity, making us all feel lucky to be part of his hilarious and romantic vision.

Dear Ruthless, 

I love going to my college reunions. I escape the family for a few days and catch some rays at my West Coast alma mater. In recent years, though, a classmate has begun throwing their own evening party at the same time as the big Saturday night event. This year is our 25th and I’m on the committee, and I hear this same classmate is throwing another competing soiree.  My strategy has been to grit my teeth and say nothing, but now I am coming to you for advice. Should I reach out to her?

I feel these private events exploit the committee’s labor while undermining the success and fun of the reunions.

Signed,

Glum Alum

Dear Glum,

KAREN: What a dick move on part of your classmate. Talk about taking advantage of your hard work. Maybe you could send an email to the class saying that you all discourage non-official gatherings from taking place at the same time as the ones on the schedule.  If you feel like it, mention the hard work, but I would keep it simple. Have a great time.

CINDY: Don’t invite her to the reunion.

Dear Ruthless,

I have a very good, very thin friend who constantly talks about how fat she is. Including at restaurants while I’m trying to enjoy my meal. Is there any way to get her to stop?

Signed,

Losing Patience

Dear Losing,

KAREN: I encourage you to show grace in this situation.  I know it seems as if your friend is begging for attention, and she may well be, but this is probably an issue that started for her before she met you. In my deeply unprofessional and unschooled opinion, her recitation of self hate may be a symptom of OCD.  All of us are imperfect.

CINDY: I have this friend. In fact, I have several of them. I agree with Karen that insecurities can be deep seated and it isn’t our job to police them. As friends, it’s our job to help relieve them. A compliment goes a long way. When my friend complains about her body, I smile and tell her she looks fabulous. If that doesn’t work, I say, “Not as fat as me.” This usually does the trick.

Dear Ruthless,

I have a good friend who is the most generous person in the world.  If she goes on a trip, she brings me a souvenir; if we get together for dinner, she will get me an ice cream or charming scarf. She is exceptional about birthdays and Christmas gifts.  I am not good at this stuff. If someone has a party, I’ll bring a hostess gift. Likewise, if she is going through a hard time or has something to celebrate, I gift accordingly. Do I have to match this friend gift for gift? P.S. It’s not a money thing.

Signed,

Gifted Up the Wazoo

Dear Wazoo,

KAREN:  I have this exact friend, and I, too, am terrible about reciprocating.  But I believe that this is how my friend expresses her affection for the people in her life.  She’s not waiting for a return gift.  Of course, there’s always the chance that I’m telling you this to justify my own inaction.

CINDY: I would invest in one big gift a year for this friend. Something really special. LIke a pony or an apartment.

Dear Ruthless,

My sister bought me an ugly Christmas sweater for a big ugly-Christmas-sweater party our parents throw for friends and family. The problem is that it is an ugly ugly Christmas sweater. Not cute, doesn’t fit well, not in the spirit of sisterly fashion sharing at all. Do I have to wear it this year?

Signed,

Double  Ugly

Dear Double Ugly,

CINDY: Here’s the 64,000 question: Are you and your sister close? Is there any chance this is some unsubtle sisterly sabotage? Are you in competition for the same cute neighbor who looks like Colin Firth in Bridget Jones? If so, have no qualms about getting yourself a super hot ugly sweater. If not, suck it up and wear it once, or get yourself something cute and tell her you’d already bought it for the party but will wear hers next year. She either won’t remember or won’t care next year.

KAREN: You never ever have to wear the sweater unless it will make your sister happy.  And then, you can give it to Goodwill.

Got a question in need of ruthless advice? Email Karen and Cindy at info@westsiderag.com.

Read all Ruthless Advice columns here.

Subscribe to West Side Rag’s FREE email newsletter here. And you can Support the Rag here.