Dear Roseanne, 

I’m a 25-year-old single New Yorker and I need help suggesting a threesome to my unmarried, coupled friends. What’s the best way for me to find out if they’re interested without making things awkward? This would be my first threesome, and I only want to do this with people I know, so strangers are out of the question. –Third Wheel to Threesome 

Dear Third Wheel,

OK, I confess that when I was a horny 20-something, thoughts like this may have crossed my mind a time or 30. I mean, if a handsome, dashing pirate captain wanted to ravage me by candlelight after a nice glass of wine, and he had a handsome, dashing friend who knew what he was doing…I mean, hey, we’re just talking fantasies here. But my practical advice would be to NOT make that “suggestion,” as you put it. Instead, maybe you could find a way to drift into the subject, somehow. Start with a really vague icebreaker about the concept of threesomes and see how they react; but make it about somebody else, in case they think it’s a proposition and it makes them think you’re coming in too high on the perv-o-meter. 

Dear Roseanne,

I’m the only daughter in my family, and I have an older and a younger brother. My grandmother’s beautiful heirloom plates hung on my mom’s walls for my entire childhood, until my parents retired about 10 years ago, when the plates were put into storage. So imagine my surprise when my younger brother sent me a picture of my nephew, and in the background were my grandmother’s plates! My feelings were instantly smashed; I always assumed I’d receive these heirlooms and pass them on to my daughter one day. Roseanne, should I say anything to my mom? –Crybaby Daughter

Dear Crybaby,

My answer hinges on this question: Did you ever make it known to your mom that those items meant a lot to you? Maybe no one in your family knew that this would be an issue for you. If you made your feelings known and they were ignored or forgotten, then I think you have a legitimate beef. Otherwise, the best you can do is wait for the right moment and bring it up to your brother or your mother—whoever you think will be more empathetic. Make sure to sound sad and wield the guilt wand with quiet authority. Lay it on thick! As a last resort, try asking about a way to share the items, since you always felt that they were something that belonged to the whole family. Remember, it’s all about family, and that often means not letting them drive you crazy. I hope you get some satisfaction.

Dear Roseanne,

I am a 42-year-old gal who recently became single. I still look as though I’m in my 20s or 30s, and catch men that age “checking me out” quite a bit, which is very exciting. There is one guy I’m particularly interested in, a college professor of mine who is 33. We’ve developed a flirtationship but he hasn’t made a move—probably since it’d be inappropriate, him being my teacher and all. The problem is, I’ve never asked a man out before. Then there’s the added pressure of telling him I’m over 40! I’ve always heard you should let younger men come to you, unless you want to be labeled a cougar (a term I despise), so I’m hella nervous. So how do I get over myself and just ask him out? –Reluctant Cougar

Dear Cougar,

I don’t want to be harsh, but sometimes all I can do is watch as the unflattering truth flies out of me like candy from a piñata. Chill with the “excitement” about men in their 20s and 30s checking you out. These are the same men who spend time checking out ads for inflatable sex dolls in the back of sleazy magazines, and sometimes just stare at anything in the produce department that’s roundish and larger than a grape. I’m sure you’re a knockout, but don’t get carried away. Now, getting to the meat of the matter: Don’t ask him out. You’re there to take the course he’s teaching, so just focus on that. He’s a professor, but he’s still a man, and if he’s attracted to you, he’ll find a way to make a move. Since he is a professor, he should be smart enough to find a way to do that without being unprofessional and breaking the rules.

Got a problem? Roseanne will help you solve it. Post your questions at bust.com/askroseanne.

Jason-Schwartzman-Cover-SmallThis appears in the Feb/Mar 2013 issue of BUST Magazine with Jason Schwartzman. Subscribe now.

 

 

Photo: FMHT Studios

Tagged in: threesome, Roseanne Barr, heirlooms, cougar, advice column, advice   

The opinions expressed on the BUST blog are those of the authors themselves and do not necessarily reflect the position of BUST Magazine or its staff.




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