Entertainment Dating
Entertainment Entertainment Dating

Quick and dirty sex advice: Winter edition

Bisexual phases, cuddling compromise, and holiday hookups with an ex

Hello, hot stuffs! I didn’t see you there through the ski mask and poofy down material covering 98 percent of your body. That must mean it’s officially winter in Chicago, but don’t worry, we’re turning up the heat for you in this edition of quick ‘n’ dirty sex advice (past quickies can be read here). Now pour yourself some Glogg, turn up your SAD lamp and settle in.

I’m a 45-year-old woman who recently realized my feelings toward women may not be entirely platonic. Am I too old to go through a bisexual phase?

Hellz no. Unlike shorteralls or Bud Light Lime, lovin’ ladies never goes out of style. Get on that and they’ll get on you.

Short version: My girlfriend likes to cuddle a lot. I need space in order to sleep. How can I get it without hurting her feelings?

Wait, wasn’t this a “Friends” episode? You’ll just have to wait until the show comes on late-night TV to find the answer. Or! Cuddle compromise. Allow your girlfriend a cuddling grace period before you turn over and ignore her. If you’ve given her a proper orgasm, she should be asleep before you know it and you can go about dreaming of Sears in peace.

How do I weather the awkward and inevitable: “So when are you two getting married?”

“As soon as I get the Facebook notification.”

My boyfriend and I have sex regularly and I go down on him a lot. But, he doesn’t return the favor. Once he was down there for about 20 seconds, but that’s it. How do I talk him into being more giving?

Well, you could get all sexy-stalemate on him and stop giving him blow jobs until he straightens up and flies south. But, the withholding option gives me the sads too. Tell him what your needs are--they are pretty routine, after all. It’s not like you’re asking him to get calf implants or install a robo-sex jacuzzi in your bedroom. If he refuses to compromise, then send him to the North Pole without a glowing-nosed caribou to guide him.

My awful six-month relationship ended last month, and the woman in question has been emailing and calling me, asking to remain friends. I can’t see us being friends right now, but is a holiday hookup out of the question?

No, but I’d advise you to seek other, less awful and more emotionally distant booty calls. It hasn’t been that long, you don’t want to be friends, and your grief is fresh. Pick a different ex, or a concerned yet flirtatious friend. It’s like I always say: “A friend in need is a friend in me.” Happy ho-lidays!

Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to redeyedating@gmail.com.  Need to give your dating life a boost? Sign up for RedEye Dating.

Want more? Discuss this article and others on RedEye's Facebook page

Copyright © 2015, RedEye
Related Content
  • Lollapalooza style portraits

    Lollapalooza style portraits

    Concertgoers pose at the three-day fest in Grant Park.

  • Lolla day 2: Best and worst, plus superlatives

    Lolla day 2: Best and worst, plus superlatives

    And just like that, there’s only one day left of Lolla. Here’s what stood out to us from day 2. Best: The Tallest Man on Earth: Maybe it was just a right-mood, right-set situation, but boy this was the perfect mid-day act to take a breather, sit in the sun, and just chill and listen to and enjoy....

  • 50 Cent at Parliament and Wyclef Jean at The Underground

    50 Cent at Parliament and Wyclef Jean at The Underground

    Shots in The Dark at Parliament Nightclub with 50 Cent and The Underground Nightclub with Wyclef Jean and Joey Fatone July 31st

  • Lolla day 1: Best and worst, plus superlatives

    Lolla day 1: Best and worst, plus superlatives

    One day down! Here’s the best and worst we saw at Lolla on Friday, plus a few superlatives from day 1. Best: Anyone who knows me knows I was bound to pick Paul McCartney as my favorite act of the day. The Beatle came out and gave it his all with more than two hours of hits, tributes and jokes about...

  • Lolla day 1: Let's just rename it Paul-apalooza

    Lolla day 1: Let's just rename it Paul-apalooza

    What can you really say about Sir Paul McCartney, the former Beatle, pop music pioneer, worldwide cultural icon, and all-around great guy, that hasn't already been said? I mean, seriously. With the Beatles changing music for the better, becoming a pop culture institution and being "more popular...

  • Aldermen looking to stop stores from getting around plastic bag ban

    Aldermen looking to stop stores from getting around plastic bag ban

    Chicago's ban on plastic bags starts to take effect at many big stores Saturday, but an alderman who helped craft the law already is talking about changing it in order to thwart a few large retail chains that he says are trying to skirt the new rules.