Photo Credit: Allen Halas
Ruthie
Dear Ruthie,
Two years ago, I fell for a guy who was down on 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 get into details, but due to my professional life, I felt we couldn’t live together. That said, I put him up in an apartment and gave him a monthly allowance to help him get on his feet.
The flame has now died between us, I’m sure he’s seeing other men and he hasn’t gotten his life together like I had hoped. I’m still paying his rent and allowance, and there’s little else between us. How do I end this cycle I’ve gotten myself into?
(Signed)
Daddy-O
Dear Sugar Daddy,
I have a credit card bill with your name on it! Listen, Daddy Warbucks, you started this relationship like a business transaction so end it the same way. Let this guy know that you need to move on, and that you’ll be ending this agreement. Give him fair warning, say a month or two, and 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’ve enjoyed one escort regularly for 10 months, but our visits became less frequent. He started messaging me saying that he was in love with me, and that he wanted to date.
Our “dates” are just sexual trysts that he wants to be paid for. He says he’s in love with me, but he expects cash for our dates. He says that because escorting is his only job, he needs to be paid when we’re together as he would otherwise be out making money with clients.
I’d like to believe he has feelings for me, but this doesn’t seem right. My friend says (this escort) is taking advantage of me in the name of love. What do YOU think?
Thanks,
Generous Guy
Dear Guy,
You know that gut feeling you get sometimes? Well, sugar, this is the time to listen to your tummy. Something doesn’t feel right here because it’s not. I’m not going to speak for the escort, but if he loves you, he wouldn’t charge you for his time.
I know it’s hard, but you need to stop writing a romance story that’s actually a piece of fiction. Either accept it for what it is or tell him you won’t be contacting him anymore. There are a lot of lovely guys out there. Go find one who’s not a hooker!
Dear Ruthie,
I have a fetish for bears. I love big, hairy men but the feeling doesn’t seem mutual. In Milwaukee, it seems that bears only like other bears. As a small, hairless twink, I’m left lonely and horny. I don’t want to be with anyone but a bear. How can I turn their heads my way?
(Signed)
Bear Chaser
Dear Goldilocks,
Speaking as someone who goes to Bear Week in P-Town nearly every year, I can say that Bears are some of the friendliest guys around. From Milwaukee and Chicago to Boston and Mexico, I have consistently found this community to be happy, accepting and awesome. Sorry that you haven’t had much luck in love but keep the faith! Your pappa bear is just around the corner. Be yourself, remain open to love and stay friendly. A hairy, bear-y love affair is sure to come your way.
Ruthie’s Social Calendar
February 17 & 18—Virtual Love is Love LGBT & Allies Wedding Showcase: The team at the Wisconsin LGBT Chamber of Commerce helps you plan your special day with this online offering. Check out the vendors, suppliers and others who promise to make your wedding shine when you register via the events page at www.wislgbtchamber.com .The cyber showcase runs 4-6 p.m. both days.
February 20—Masquerade Carnival at Home: Join team members from Madison’s Crucible nightclub as they host a Twitch event sure to liven up you 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 9 p.m. dance party at www.twitch.tv/crucible_madison.
February 24—Networking Online Happy Hour: Grab a beverage at home and settle in for some virtual elbow rubbing when you attend this monthly happy hour of business owners from the LGBTQ+ community. The 4:30-5:30 p.m. social is free and open to all, but you need to register first via www.wislgbtchamber.com.
Have a question for Ruthie? Want to share an event with her? Contact Ruthie at DearRuthie@ShepEx.com.
