Category: Ask Her

Ask Her: Living in a BDSM relationship

Dear Bailey,

I have just finished the Fifty Shades of Grey series.  Given the runaway success of the novel and its sequels, particularly among women, do you think bondage and consensual S&M can play a healthy role in a successful, long-term relationship? I would really like to explore this type of relationship with my husband, but my friends tell me I’m twisted for wanting it.

-Laura B; San Diego, CA


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Ask Her, Vol. 9 Sex With the Ex

Dear Bailey,

My ex-girlfriend and I broke up about 4 mos ago.  We are both still single and have no desire to get into a relationship.  She recently called me at midnight wanting to have no strings attached sex, and I said yes, and now we are having sex weekly without a relationship.  I don’t mind having NSA sex, but I’m afraid she might get attached again and I don’t want things to get weird.  What should I do?  

-Jack D, Los Angeles  

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Ask Her, Vol. 8 The Brian Howard Show

Have you ever wondered what I sound like in person?  What I think about anal sex? Now you can find out!

Today I had the pleasure to be a guest on the Brian Howard Show in Los Angeles California.  I was the resident relationship expert and had an amazing time.  I was in studio with the funny and talented Brian Howard, the sexy and unkillable Jennifer Lynne, and the amazing Jack Dagger who (no joke) was rated as one of People Magazine’s 100 sexiest people, and has appeared on Conan O’Brien and the Tonight Show.

Special Thanks to The Texifornia Tamale Co, located in Blue Jay, CA for donating the most incredible food we’ve ever eaten.  I’m serious.  If you are in Southern California, stop by Lake Arrowhead/Blue Jay and give them a try.  You will be glad you made the drive. It’s road trip worthy. Give em a call at (909) 336-1200, and tell them that Bailey Ryan sent you.

Additional thanks are due to A Shot Above Bartending for supplying the Jello shots for the SEX CONTEST on the show.  Listen now to hear the fun and games!  Give them a call for ALL you bartending needs.

Listen to me talk about anal sex, orgasms, and the truth about open relationships:

Visit: The Brian Howard Show, featuring Bailey Ryan and listen now!



Ask Her, Vol 7. Wet T-Shirt Fun

Dear Bailey,

My g/f has an amazing body, and has in the past been somewhat shy about showing it off in public. Recently, she is seriously starting to consider participating in a bikini or wet T-shirt contest. I’m somewhat conflicted; part of me would be proud to be in the audience and support her and finds the idea very hot, and a little part of me is jealous at the same time at all the attention she would no doubt receive. Do you think this would strengthen the relationship or weaken it?

-Lance M; Milwaukee, WI Read more

Ask Her, Vol 6. Hot Oral Sex

Dear Bailey,

My girlfriend loves it when I go down on her, but says she hates giving head because she feels too submissive. Is oral sex a submissive act?

-Oscar G, Victorville, CA

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Ask Her, Vol 5. The Importance of Kissing


Most of the questions I receive are from men looking for advice, but this one came in from a woman in Los Angeles and it spoke to me, so I felt the need to answer it here. Guys, this one is important! It may save your relationship someday!


Dear Bailey,

My boyfriend and I have been together for about 6 months, and he doesn’t like to kiss me.  He says he’s never enjoyed it and not to take it personally, but I love kissing so much that I feel I’m being cheated. What should I do?

-Buffy, Los Angeles, Ca


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Ask Her, Vol 4. Sexy Bedroom Role Play

Dear Bailey,

My wife just told me she wants to role-play in the bedroom.  I’ve never done this and think it’s a little weird.  Is she the weird one or am I?

Phillip L.  –Hollywood, CA

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Ask Her, Vol 3. Hot Threeway Sex


Dear Bailey,

My wife likes girls, and we recently hooked up with a girl and we had a good time.  Is this a good idea, and should we do it again?

-Daniel Nieves  @dnievesfilms


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Ask Her, Vol 2. Attracting the Crazies

Ever have one of those feelings?


Today’s question comes from twitter.  Being a common occurrence, I felt it should be addressed:


I’m only attracted to crazy women. What’s wrong with me?

-Aaron J. Marko @DinkCheney


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Ask Her, Vol 1

Dear Bailey,

I always seem to upset my girlfriend over the smallest little things.  I really don’t try to, but just the other day she became almost irate over nose hair. How do I get her to chill out about things like this, and are there any other pet peeves women have that I should know about?

-James H, Salt Lake City, Utah

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