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Answering Age-Old Questions

Nov. 8, 2016
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Dear Ruthie,
How long should I date my boyfriend before proposing?


Dear Rudy,
If he’s over 85, wealthy and growing more pale by the day, I’d say now! Do it now! Otherwise, wait a year. You need at least 12 months under your belt to make sure you know this person well enough to start building a future together.

Dear Ruthie,

My friend is 38 and wants to do drag, as in being in drag shows and pageants. I think he’s too old and wasting his time. What do you think? You’re old.


Dear Business,

First of all, fuck you. Secondly, it sounds like your friend has a yen to perform, and there’s no age limit on that. Be a good buddy and encourage your friend to fulfill his dreams, no matter what they are. Suggest he start out slow, perhaps performing at a talent night or charity event.

Dear Ruthie,
I’m interested in a guy 27 years my junior. Is that too young for me, you think?

Papa Bear

Dear Pervert,

What could possibly go wrong with this scenario? (Insert eye roll here.) Listen pops, if you want a nutty roll in the hay, go for it. If you want something serious, look for someone your own age. Try keeping the age difference to no more than 10 years between the two of you.


Nov. 9: Bridget Everett at Turner Hall Ballroom (1040 N. Fourth St.): If you haven’t seen Amy Schumer’s bestie perform in P-Town, New York or any other LGBT hot spot, now is your chance! A cross between Divine and Bette Midler (of her bathhouse days), this saucy songstress is sure to dig a well in your heart and climb right in. Brash, bawdy, bitchy and fabulous, Bridget’s “Pound It” tour is one for the books! Tickets to the raunchy 8 p.m. comedy concert start at $25. (The doors open at 7 p.m.)

Nov. 10: Pride Movie Night at UW-Milwaukee LGBT Resource Center (2200 E. Kenwood Blvd./Union WG-89): Stop bitchin’ about your inability to meet new people! This popular LGBT movie night is back just in time for cool-weather get-togethers. What’s the movie? Who knows? That’s half the fun! Show time is 5 p.m., and you’re on your own for soda and snacks, honey. 

Nov. 10: Pie and Wine Sampling at Miss Cupcake (3801 N. Oakland Ave.): Yes, you read that correctly…pie and wine sampling. (I’ll give you a moment to collect yourself.) Join the crew at this cute cupcakery from 6 to 8 p.m. when you’ll get the chance to taste a few classic pies as well as a few new flavors.

Nov. 12: Taste of the World at American Serb Hall (5101 W. Oklahoma Ave.): My amigos from Shepherd Express serve up a smorgasbord of ethnic edibles during this 2 to 6 p.m. extravaganza. More than a dozen vendors offer specialties from various regions of the globe, from Africa to India, while dance troupes and more provide nonstop entertainment. The adults-only sampling involves a $30 door charge. 

Nov. 13: Bundle-Up Party at Kruz (354 E. National Ave.): The L/L social group Castaways MC of Milwaukee gear up for yet another Sunday Funday. This time, they’re collecting coats and winter accessories for those in need. (Think gloves, scarfs and hand warmers.) A donation gets you five free raffle tickets with prizes being awarded throughout the 3 to 7 p.m. party. Round out the fun with a beer bust and all the hot leather guys you can handle! 

Give Ruthie a jingle…er, uhm…an email. Drop her a line at dearruthie@shepex.com, and share your problems or tell her about an event she might want to share in this column.


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