Ask Wendy

dating, sex & relationship advice for the bold!

Got a question? Send it to

How Can I Tell Him?

I’d really like to see you let your new guy walk into your home with his eyes wide open to see what you really need help with because he’s actively offering to pitch in. If you’re unwilling, I still recommend the truth.

Read More »

Does Porn Play Out In Real Life?

A couple of months ago I found out that he was very much into incest porn. This is something he is extremely ashamed of. One night, after he fell asleep, I checked his history even though I told him I would respect his personal life.

Read More »

My Boyfriend is Broke, Should I Keep Him?

Does he have a plan for paying the bills while he’s investing in his passion? Do you share similar lifestyle expectations? What’s his relationship with money? Has he planned for a side job that will help the two of you make ends meet?

Read More »

How Can I Get His Ex To Like Me?

I’ve been with my boyfriend for about a year. He doesn’t have many friends and his ex-girlfriend is one of his closest friends. They “share” her dog. He loves this dog and sees his ex like a sister. I don’t have a problem with that.

Read More »

“What’s Your Sex Number?”

At the start of dating, my wife told me the number of men she’s had sex with was 3. She’s recently admitted that the real number is 40. How do I not despise her for this? She has been my best friend for a long time, but she has also lied a LOT about sexual things.

Read More »

Do I Have to Tell Him My Age?

I’ve met a wonderful man who’s 36, and he doesn’t know I’m 35 yet. He hasn’t asked for my age, but I feel he needs to know ASAP, as he might want someone younger considering I look like I’m 25 maximum. I want a husband and a family, but I’m afraid that he won’t want me because I’m too old. What if no man my age will want me anymore?

Read More »

BDSM Advice

My girlfriend and I have been together for seven years. From the beginning, I’ve been the dom and she has been my sub. Recently we had a heart to heart where she expressed she’s no longer happy being the sub, and instead wants to switch our relationship around and flip the power dynamics so she’s the dom and I’m the sub.

Read More »

Sign-up to receive Ask Wendy via email

Recent Posts


“This was without a doubt, life-changing. I had no idea that my marriage could be this intimate, fun and safe by applying what I learned. It’s been three months now, and our marriage is unrecognizable in the best ways possible. I can’t thank you enough, Wendy.”

Audrey H. – San Francisco, California

Magical & Visceral

“Why weren’t we taught this in school??? This is right on and has already transformed my relationship with my boyfriend. It feels magical and visceral. Thank you!”

Kim A. – Sedona, Arizona

A Bright Future

“Thank you, Wendy, for your generous insight and compassionate understanding of men. I joined your workshop with my mother. We are desperately trying to break eight generations of bad relationship dynamics with the men in our family. I’m sure that we are on a different path and look forward to a bright future being happy and healthy in our relationships with all men in our lives. All my love.” Hailey B. – Seattle, Washington