I’m 32 years old, and until a few months ago I was a hopeless womanizer. I seduced countless women, had threesomes, swapped partners and even made amateur porn. I keep a dresser drawer full of trophy panties. But a few months ago I met a woman I’m so taken with that I have stayed committed and monogamous. I want to propose to her. Should I get rid of the panties and not tell her about my past, or should I come clean and tell her everything?J.D., Jacksonville, Florida

Congratulations on your wild youth and your newfound love. We suggest you give the relationship at least a few more months before you propose. If you still feel the same way after the relationship has been road-tested and the novelty has subsided, you should come clean so that in your married years you’ll be able to come with a clean conscience.


This question is from the NOV 2014 issue of Playboy. To read the rest of this Advisor column, click here.

For answers to reasonable questions relating to food and drink, fashion and taste, and sex and dating, write the Playboy Advisor, 9346 Civic Center Drive, Beverly Hills, California 90210, or email advisor@playboy.com. The most interesting and pertinent questions will be presented in these pages each month.