Cigar Lifestyle
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Starting this month, Cigar Advisor is proud to introduce Sondra Theodore, who pens this new relationship advice column. Sondra is a former Playmate who enjoyed a 5-year relationship with Hugh Hefner and made her cover debut in the December 1977 issue. Eventually, Sondra left the Playboy mansion, married, and raised two children. Sadly, her marriage ended in divorce, yet, as a result, she is a highly qualified to speak on any number of relationship topics. We hope you enjoy this new addition to our magazine, and feel free to ask Sondra a question on your own!

Dear Sondra,

I’m a 25 year-old U.C. Berkeley graduate working in the high tech sector, and I want to date older women. Most of the girls around my age are so immature I find it difficult to relate to them. I think a woman with more “experience” would be better suited for me, like someone in their 30’s or 40’s. Do you agree?

– R.J. in Mountain View, CA

Dear R.J.,

As far as older women go, yes you are wise to want the company of them. They are, for the most part, done with the game playing and petty jealousies. They are more confident sexually and usually know exactly what they want. It would take a very mature younger man to realize just what he was getting into, and how best to approach and deal with an older woman. You sound like you know what you want. Go for it! I like to hear about men liking the older woman for a change. After all, we have much more substance and class at 30-35 than we did at 20 -25! Smart young man that you are, it’s true that some things do get better with age. ~S

Dear Sondra,

I’ve been dating a woman for almost two years and she has a serious jealousy problem. Some of the girls I dated in the past have remained friends, so I still keep it touch with them. This drives my girlfriend crazy and usually leads to an argument. I’ve told her time and again that these women are just friends and she has nothing to worry about, but it doesn’t seem to help. How would you suggest I handle the situation?

– Spencer in South Carolina

Dear Spencer,

A jealous woman is not a fun woman, nor is she a happy one. Try letting her know she is number one and the love of your life. More often little gestures speak a thousand words. Bring her home some flowers for no reason at all. Or leave a love note on her pillow or car windshield before sneaking off to work. She will love you for thinking about her, and it will make her feel special. Try doing these little things on a regular basis and see how the jealously stops. Women don’t like it when their man has time for other women when their own needs are not met. Women really are very easy to please if you just know the right approach. Just saying.


Dear Sondra,

Ever since my wife and I had our third child about 2 years ago, our sex life is not what it used to be. She’s still very attractive and keeps herself in excellent shape by working out at our community center gym. Now she goes to bed early, so by the time I join her, she’s asleep. If I try to arouse her, she just says she’s too tired and turns over. Though I would never consider having an affair, I’m almost at my breaking point. What can I do to get the romance back in our relationship?

– Horny in Hartford, CT

Dear “Horny,”

I remember those days well. After having a baby on your hip all day, not to mention breast feeding and being spit-up on half a dozen times a day, then chasing after another little one, having your husband reach for you after you have blissfully slipped into blessed sleep, you are putting your very life at risk! If you want the romance back, then create it. Call her up and tell her she has the night off; that you got a sitter and you are taking her to a fancy restaurant. Let her be pampered for a change. Tell her she is beautiful over a candle light dinner and champagne. You won’t have to ask-she’ll be all over you-maybe even before you make it home!

Don’t make sex just one more thing she has to do; make it the one thing she can’t wait to do!

~ S

Dear Sondra,

My girlfriend grew up in a very protective family, so she didn’t have much dating experience, and I was her first. We’ve been together for almost six years, and recently got engaged. She’s really good at oral, and says I give her great orgasms during sex, but when I bring up doing something like anal, or bondage, or bringing in another girl, she freaks out. If I’m going to spend the rest of my life with her, my hope is that she will become more adventurous. Am I headed for disaster?

– J.B. in Houston, TX

Dear J.B.,


~ S

Dear Sondra,

My girlfriend is really hot. Great body, beautiful face, and when we first met I thought she was a model. Actually, she’s a dental hygienist. The thing is, she wears clothes that really show-off her body, and wherever we go, other guys are always staring at her. If we’re at a club and I leave her for a few minutes, when I return some guy is hitting on her. I’m pretty good at diffusing the situation, but at 5′ 7″ I’m not a big guy. We’ve only been dating for about three months, and so far things have been going good, but I’m always aware of these other guys checking her out and it makes me very uncomfortable. I’m also afraid I could lose her to someone else. What can I do to keep my sanity?

– Kenny in Port St. Lucie, FL

Dear Kenny,

Stand tall and be proud of the fact your girlfriend is hot. Don’t feel insecure when confronted with her admirers; remain confident and without saying a word they will get the drift she is already taken-and that she is yours! She will find that very attractive and be even more into you. I know this for a fact, my mother was 5’7″, my father was 5’5″, and she thought he was the tallest man in the room!


Have a relationship question for Sondra?

Email her at [email protected]

Unless specified otherwise, names will be displayed anonymously using your first name or initials, and your city or state. Please keep it clean. Vulgar questions or lewd personal remarks will be rejected.

Follow Sondra on Facebook.

The opinions stated in this column are those of Sondra Theodore, and do not necessarily reflect the opinions of


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Sondra Theodore

Sondra Theodore

A native of San Bernardino, CA, Sondra Theodore is a former Playmate who made her pictorial debut in 1977. She lived at the Playboy mansion with Hef for over five years, where she was known by the nickname, "Baby Blue." Hugh gave her the name because the Barry White song of the same name was the song they danced to on the night they first met. Eventually Sondra left the mansion, married, and raised two children, a son, Taylor, and a daughter, Katie. Some 10 years later, Sondra and her husband divorced. An accomplished pianist, Sondra holds a degree in Dramatic Arts from U. Cal. San Bernardino, and has a passion for refurbishing furniture, turning the ordinary into the extraordinary. Having lived an extraordinary life, herself, Sondra currently enjoys a quiet, comfortable life in Los Angeles with her two dogs, Charlie and Jack.

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