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Daddies & Escorts & Bears…Oh, My!

Dear Ruthie,

Two years ago I fell in love with a guy who had lost his luck. He was a hardworking, good, honest person. Granted, he was 31 years younger than me, but we enjoyed each other. I won’t go into details, but because of my professional life, I felt like we couldn’t live together. That is, I took him to an apartment and gave him a monthly allowance to help him get on his feet.

The flame has now gone out between us, I’m sure he sees other men and he hasn’t brought his life together the way I hoped. I’m still paying his rent and allowance and there is little else between us. How do I end this cycle that I got drawn into?



Dear Sugar Daddy,

I have a credit card statement with your name on it! Look, Daddy Warbucks, you started this relationship like a business transaction, so you end it the same way. Let this guy know you have to move on and that you are going to end this arrangement. Give him a fair warning, say a month or two, then cut the chord in every way.

Dear Ruthie,

I’m no stranger to paying for sex. I’m an older man with a healthy sex drive and it’s just easier to pay hot guys for fun. I enjoyed escort regularly for 10 months but our visits became less frequent. He started telling me that he was in love with me and that he wanted to date.

Our “dates” are just sexual trysts he wants to be paid for. He says he’s in love with me, but he’s expecting cash for our data. He says that because escorting is his only job, he has to be paid when we’re together, otherwise he would make money with clients.

I would like to believe that he has feelings for me, but that doesn’t seem right. My friend says (this escort) is taking advantage of me in the name of love. What do you think?

Many Thanks,

Generous guy

Dear guy

Do you know the gut feeling you get sometimes? Well, sugar, this is the time to listen to your gut. Something doesn’t feel right here because it isn’t. I won’t speak for the escort, but if he loved you he wouldn’t charge you for his time.

I know it’s hard, but you have to stop writing a love story that is actually a fiction. Either accept it for what it is or tell him you won’t be contacting him again. There are a lot of nice people out there. Find someone who is not a hooker!

Dear Ruthie,

I have a fetish for bears. I love tall, hairy men, but the feeling doesn’t seem to be mutual. In Milwaukee, bears just seem like other bears. As a small, hairless twink, I’m lonely and horny. I don’t want to be with anyone but a bear. How can I turn her head my way?


Bear hunter

Dear Goldilocks,

Speaking as someone who goes to Bear Week in P-Town almost every year, I can say that bears are some of the friendliest guys out there. From Milwaukee and Chicago to Boston and Mexico, I’ve found this community to be happy, acceptable, and great. Sorry you weren’t very lucky in love, but keep the faith! Your papa bear is just around the corner. Be yourself, stay open to love, and stay kind. A hairy, bearded love affair is sure to get in your way.

Ruthie’s social calendar

February 17th and 18th – Virtual love is love LGBT & Allies Wedding Showcase: The Wisconsin LGBT Chamber of Commerce team will help you plan your special day with this online offering. Check out the vendors, suppliers, and others who promise to make your wedding glow when you register through the events page at The cyber shop window runs from 4 p.m. to 6 p.m. on both days.

February 20 – Masquerade Carnival at Home: Join team members from Madison’s Crucible nightclub and host a Twitch event that is sure to liven up your week. Known for drag and burlesque performances, as well as cosplay events and alternative theme nights, Crucible continues to celebrate the night on Twitch TV. Join the free dance party at 9pm at

February 24th – Networking Online Happy Hour: Get a drink at home and enjoy the virtual elbow rubbing as you partake in this monthly happy hour with business owners from the LGBTQ + community. The social from 4:30 p.m. to 5:30 p.m. is free and accessible to everyone. However, you must first register via

Do you have a question for Ruthie? Would you like to share an event with her? Contact Ruthie at