Dear Sammy: The Go-To Sexpert For Many
Welcome to my inaugural installment of “Dear Sammy!”
In the early 80’s I dropped out of The High School of Performing Arts after graduating 9th grade to become an International teen model. I never got my High School Diploma. I have no degrees, or masters, or bachelors, or other titles that relate to education, just life experience. Despite all of that, for over a decade I’ve been dispensing sex, dating and relationship advice on radio, television, and in various publications, but I’ve never had my own weekly column. That is until now!
I’ve been the go-to therapist for many of my friends for my entire adult life, and have spent countless hours counseling and advising them by phone, and in person. I recently started charging for my time, and turned my problem solving abilities into a burgeoning Life Coaching business.
My unofficial training started back in 2001 when I co-hosted the nationally syndicated network talk show, “Men Are From Mars… Women Are From Venus.” Based on the bestselling John Gray novel, the morning show explored the complexities of interpersonal relationships between men and women.
For several years I was a reporter on Playboy channel’s Sexcetera, where I traveled the country interviewing various people, their sex practices, and lifestyles. I’ve also executive produced, produced, and appeared in several cable series devoted to the dating genre.
Currently I host The Single Life on Vivid Radio SiriusXM 791, and www.vividradio.com every Thursday and Friday, live from noon – 1pm PST. And for the past 5 years I’ve been co-hosting once monthly the It’s Time S&R (Sex and Relationships) Show with UFC Announcer Bruce Buffer, and Sherdog Radio’s TJ DeSantis, now on Fox Sports online.
I consider myself a ‘sex-pert’ based on the above qualifications, plus the fact that I’ve slept with over 500 guys. Not to mention the thousands of blowjobs I’ve given over the years. As they say, practice makes perfect. One lesson I learned firsthand is that finding someone to have sex with, or date, or marry is a numbers game. You need to play the field in order to score.
On that note, let’s get to some of your letters.
So, what’s the deal with dating these days? As a 50-year old guy, I want to find a woman more my age, but the women 40-50 are looking for guys 25-30. The men I hang out with want to chase 20-somethings. Then the 30-35 year old women want a guy my age, but they have kids, or no career, or want a sugar daddy.
Can you explain what women in each age group really want, and what ages of women a guy who is 50 should be looking for?
Hey Marc, I think an important question is where are you looking for these women? Are they online? In bars, clubs or restaurants? Walking on the street, or in a Dog Park? Working out? In a heath food or grocery store? Through your friends or co-workers? The environments in which you meet them, or find them hanging out will determine where their heads are. I’d start frequenting the types of places that you see your dream chick being. And you should be pursuing your hobbies and interests where people congregate. Personally, I have met the loves of my life in the most unlikely places.
You wrote that you want to be with a lady more your age. Just keep in mind that the older gals are going to have way more baggage than the younger ones. There’s also a possibility that she’ll have debt, kids, and physical or emotional scars. On the flipside she’s probably “been there, done that” and knows exactly what she wants out of life, and in her partner. Chances are she’ll be better at sex than someone half her age, and more focused on pleasing you than herself. You need to decide which qualities are more important to you, the good or the bad.
I just turned 49. I can most certainly tell you that at my age, I don’t mind fucking a 25-30 year old, but I’m not looking to have a relationship with one. I think it’s individual, according to the stage the man or woman is at in their life mentally, emotionally, and financially. This determines whether or not they want to play the field and stay single, or settle down when they meet the right one. Anyone can do anything if they are ready. Age is a state of mind, not a number.
You can make generalizations about age, but you’d be eliminating a portion of the population where “the one” may be waiting for you. Just put yourself out there, use your common sense, don’t hurt anyone, and have a good time.
My platonic lady friends won’t let me date their girlfriends, sisters, or cousins. They change the subject anytime I ask. I’m a good guy! I care for my ailing dad, and I can cook.
Well Graham, I tend to agree with your lady friends. I don’t care how many redeeming qualities my guy friends have, I’m still not setting them up with my girlfriends, let alone with one of my family members. First of all, my family is nuts. Second, so are my girlfriends. I don’t want to be responsible for what happens when the shit hits the fan, and invariably it always does.
It’s a lot of pressure hooking two people up that you care about. Especially when it doesn’t work out. Either you get blamed for setting them up, or you get dragged in to play mediator. You end up having to listen to both their versions of every good and bad thing that happens to them as a couple. And forget about choosing sides in an argument. Like Switzerland, you have to be diplomatic and maintain a neutral stance. God forbid you end up in the middle of their drama; you can run the risk of losing both relationships. For these reasons and more I just say, “No” when someone asks me to play matchmaker.
If you love a guy, but he has a small penis, could you deal with it? He’s a regular guy, he’s got a job – but isn’t rich, he remembers your birthday, and he’s good at oral and digital stimulation.
He’ll even wear a strap on if you need that. However, could you deal with getting him off?
Hey Jon, that’s a great question. I admit it; I’m a size queen. But not in the way you’d probably think. I do care about penis size – I care if it’s too big for me. I don’t like pain, so for that reason I prefer a man less-endowed downstairs. Personally, (and I represent 85% of the female population) I love an average sized dick, in the 5” – 6” range. I’m a tall girl (5’9”), but I’m a small girl on the inside.
It all comes down to how big the canal of the chick you’re fucking is. If she’s got some cavernous hole, and you’re on the under 6” side of the ruler, you will feel like a hotdog in a hallway. Think of it like fitting two puzzle pieces together. You’re not going to join the little corner section to a big chunk from the middle. My advice is to find a petite lady with an even tinier vagina, to make you feel like the stud that you are.
At the end of the day, I get off on the man – not his member. I’ve dated guys with every shape, size and deformation imaginable, but I make it work if I like him. I don’t need a strap-on, or toys etc. to turn me on. Every man that I’ve slept with that was on the smaller side made up for it in other ways. Not to mention, you realize where our G-Spot is located, right? Go inside any vagina about 2” – 3” then push up. Hello! You’ve just met my vaginal orgasm. Like I said, 5” is right up my alley. And most others, too.
I saw your Facebook post about your new advice column, and I need some! My wife (after being together for 14 years) has decided she doesn’t know if she wants to be together anymore.
We have been living apart, each one of us with one of the kids since last June. She still doesn’t know what she wants, claims she isn’t banging anyone, but yet doesn’t seem to want to have sex with me. We hang out every weekend, and we talk and text each other all day, but I’m really starting to feel like this is a one way street.
I have tried talking to her about this, and all she says is, “There’s no divorce paperwork filled out.” I just feel like my life is on hold while I’m waiting for her to figure out what she wants! Sammy what the hell I’m I supposed to do?
Keith, I feel for you. I wish you had mentioned your wife’s age. If she’s in her 30’s – 40’s, she can be going through either perimenopause, or menopause. The symptoms range from vaginal dryness and discomfort during sex, to mood swings, fatigue and loss of libido.
When women go through menopause (men-o-pause), we literally push the “pause” button on men. And not because we want to. Half the time we don’t know why we’re feeling the way we do, but I can tell you our hormones play a huge role in our indecisiveness. We don’t feel attractive. And most times sex hurts.
If this is what’s going on with her, she may be in denial, or she may be dealing with it privately. Sometimes it’s hard to come to terms with the fact that we are aging, and our bodies are changing. If this isn’t her problem, then perhaps she’s simply grown apart from you. 14 years is a long time to spend with one person, especially if she met you when she was young, or she had limited sexual partners prior to being with you.
My advice is to seek out a couple’s counselor. The only way to get to the bottom of these issues is to talk about them in a safe, non-judgmental, and supportive environment. If she were not willing to discuss them with you, then I would take your power back, and consider moving on with your life.
I’ve got a question for you that I have no clue what to do… I met a young lady about 4 1/2 years ago. We got along great, and wanted to turn our friendship into more. Anyways, she ended up moving away to northern CA, but we did keep in touch.
Several months passed, and I met someone, who I’m still dating currently. I just recently found out the girl from northern CA is moving back to be close to her family, and me. I like the girl I’m seeing, but also like the girl returning to my area.
What is a guy to do? I’ll take any advice you’ve got. Thanks, your friend.
Hey Tony, I’m sure you’d love to have your cake, and eat it too. Who wouldn’t? In a perfect world you’d be able to date both women to see whom you like more. But that’s not very fair to the girl you’re currently with, that you’ve been seeing for the last four years.
If you still have feelings for the Nor Cal girl, is it possible you see her as “the one who got away?” You didn’t tell me how long you dated her, but according to your math it doesn’t seem like it was for more than a few months. Was your connection purely sexual? Do you feel like she was your soul mate? What is it about her that you’re still attracted to?
You need to do some soul searching. Is this is a “grass is greener on the other side” type situation? Are you in love with Nor Cal girl? Or, are you using Nor Cal girl as a way out of your current relationship? Only you know these answers. I recommend that you have an in-depth heart-to-heart with both these women, and figure out what you want.
I always say, “If you’re dating one person, but you’re thinking about being with another, then you need to break up.” If you were really into your present girlfriend, you wouldn’t have feelings for anyone else. Don’t lead her on. Don’t waste her time – or yours. You only have one life, and you need to be with someone that makes you happy.
Send your sex, dating and relationship questions to email@example.com.