Over 50, Single and Dating – What You Need To Know


Imagine a woman over 50, who suddenly finds herself single again and longing for companionship. In my case I had been without sex or any sort of affection for almost two years. I craved connection. I wanted sex. But, I had no clue of how to go about finding what I wanted. I turned to an online personals site.

That was 12 years ago. Separated and moving slowly towards divorce, I was determined, impulsive, naïve and hampered by my desires to find a man. The results were humorous, pathetic and exhilarating–in equal measure. My first sexual encounter was disastrous. He had a tiny half-erect penis that he tried, repeatedly, to shove in while saying something about forgetting how small it was…. Horrifying. Undoubtedly the worst sexual experience of my life.

I only had one date with the man who turned out to be married and sleeping with 3 other women—I was to be the fifth in his stable. Several years later I saw his photo in the paper—he’d been convicted of trying to murder his wife.

The Doctor who started the date by asking to wear my bracelet so he could ‘get’ my energy. I agreed to wear his cheap rubber watch during our (one and only) coffee date.

The list goes on.

The Challenges of Over 50 Dating

Entering the dating pool, particularly online dating, is new to many of us over 50. How do we get started, what is it like to go out on a date? And sex? Yikes. Getting naked in front of a stranger after all those years, baring our saggy boobs, stretch marks, and flabby tummies. It’s daunting.

There are so many things to think about—like sexual transmitted infections. We may have no idea how to ask the right questions. Many older women can’t even imagine having a conversation about sex in general.

Talking to a stranger, arranging that first date, figuring out what to share and how soon. Handling the rejections. It’s a lot to figure out in the beginning. We were savvy in our former lives, but when it comes to starting over as a ‘single’ woman we may feel overwhelmed. Where do we turn for help?

What The Over 50 Woman Wants to Know About Online Dating

A search for guidance on the internet will turn up many ‘experts’ eager to provide answers. Love Coaches will help you clear up your daddy issues or talk about the Laws of Attraction. Or maybe you want to fork out big bucks for an hour of personal coaching to get in touch with your fabulous self? You can find tips on how to dress younger, dye your hair, reverse the aging process and flirting.

For example, John Grey of Men Are From Mars, Women Are From Venus fame offers some flirtatious questions to use on a potential date. My favorites: “What was your ex thinking when he/she let you go?” or “What is your favorite ice cream flavor and why?” Really? An opening gambit that has me talking about my love affair with Ben and Jerry? Or leads to an angry diatribe about the ‘ex’.

Treat me like an intelligent woman. Don’t assume I’m going to change my appearance and lifestyle to attract a husband. Don’t tell me putting scented candles in my bedroom will make a man swoon with desire for me—though the dim light might hide the stretch marks on my stomach.

Don’t assume that I’m looking for a husband.

Educate me about sexy. Tell me how to find a reputable confidential lab for STI testing. And explain why I need to worry about herpes when I’m 65. Talk to me about dealing with erectile dysfunction. Show me some of the best sex toys sites on the internet and which toys I might enjoy on my own or with a partner. Let’s have more websites focused on sex for older women—my needs are somewhat different from a 25 year old’s. What about lingerie that won’t make me look like a whore?

Show me how to avoid predators, scams and unpleasant men I’m likely to find in an online dating site. Share some tips on making the first phone call, or scheduling my first date with a complete stranger.

Don’t talk down to me. Don’t tell me how many frogs I have to kiss. Don’t insult my intelligence with perky little pep talks. Don’t send a married 26-year-old man to tell me, a 57-year-old woman, what I need to do to attract the right man.

Women want and expect relevant, useful, intelligent advice, information and resources. We want straight talk that acknowledges our capabilities while offering legitimate support as we begin online dating and move into relationships.