Cocktails Lipstick and Love, Advice from Wilma Fingerdo

America’s Sweetheart Wilma Fingerdo

Welcome everyone to my first love and advice column. Our fans have been so good to us over the years that I just wanted to give a little something back to the community and this is as little as it gets. As I’m writing this I am poolside in sunny Florida sipping a mojito and dictating my new column to our pool boy Alejandro. I’m doing everything in my power to give this sweet boy an odd job or two to help him work his way through pet grooming school and you know what, it’s harder than you think to shape a poodle tail in to a little ball. Poor Alejandro’s always seems come out phallic shaped, I know he will keep working on it until he gets it right. If you need advice on love, life or how to mix that perfect drink don’t hesitate to write me, wilma_fingerdo@comcast.net.

Dear Wilma, I’m a young gay man in Northwest Indiana area and I’m wondering where I can go to meet other single men that doesn’t involve apps or online dating? Signed, Lonely Homo

Dear Homo, Northwest Indiana has a very open and friendly group of gay men that host events, and there’s no need to go alone! Have you ever heard the phrase, “Don’t go stag, drag the hag?” Get one of your lady friends and head out to Dark Star on Thursdays for Karaoke, Or you can follow the OUT in NWIN’s Facebook page for our local drag shows that are hosted in Michigan City, Portage and Winfield. Good Luck! XOXO

Hi Wilma! Have you ever had a doctor cup your balls and fondle them? Is this normal? What are they checking for? Thanks, Touched and Confused

Dear Touched, Heavens NO! I’m a lady for fucks sake. I’m no Dr. Quinn Medicine Woman, but I believe that this will help to determine if you have a hernia. It’s either that or your doctor thinks you’re cute. XOXO

Dear Wilma, My boyfriends penis is really thick, do you have any tips for me? Sincerely, Ouchy

Dear Ouchy, Have you heard of booze and lube? That’s how I do it. XOXO

Dear Wilma, Valentine’s Day is coming and I was wanting some input, what would you do for a first date on Valentine’s Day? Where would you take your date and how much is appropriate to spend? Thank you, Anonymous Hopeless Romantic

Dear Anonymous, My legs rise according to the dollars spent, and “the sky’s the limit!” Seriously though, I think this is going to depend on the person you’re dating. I’ve spent many Valentine’s Days at home, but we’ve also indulged in $700 dinners in the City. Why don’t you cut to the chase and ask them what they want to do? You could spend as little as $50 for some pizza, a thoughtful card and Netflix, or thousands on a night on the town. I would let your date lead the way. Regardless, I think a nice card and some flowers always do the trick! Good Luck! XOXO

Wilma Fingerdo and Welcome to the Other Side can be seen performing at Shenanigan’s in Portage on February 25th 2017.