10 Things You Should Never Do While Dating After 50

A man dating after 50, holding flowers behind his back while his date laughs in front of him.

Dating is a fun yet complicated thing. And that doesn’t change with age. The older and wiser people get, the more they know what they do and don’t want in a relationship. And while that’s a good thing, it can also make finding a potential partner a bit more challenging. Whether you’re just getting back into the dating scene or have been dating for a while, maintaining a positive attitude and being open-minded are crucial.

That said, here are 10 things you should never do, if you’re dating after 50.

Never be ashamed of your age.
Carlee Linden, an online dating expert, says many older adults struggle to accept their age and attempt to fight against it.

“However, in this day and age, there is no reason to be ashamed of your age. Instead of fighting against it, embrace it,” she explains. “With age comes a certain confidence that those younger than you just seem to lack. You have experiences that we don’t have, and you know who you are and what you like. Be proud of your age.”

Never take online dating personally and never give up looking.
The point is that if you take online dating personally, you’ll give up too soon. 

“Online dating can be fun, but you’ve got to approach it with the right attitude and the energy to see it through,”says Shirley Goldberg, founder of Midagedating.com and a dating expert for the over-50 woman. “If you’re meeting new people, which is what online dating is all about, you won’t like them all. You’re deciding who is worth your time. Therefore, rejection is a normal part of the dating process. When you’re rejected, move on.”

Never move too fast.
Dating in middle age may feel like a race to the finish, says dating and relationship expert, Amy North.  

“You’ve been single for long enough and you want to skip all the early, getting to know you stuff and jump right into the comfort and security of a relationship,” she explains. “But this can often put a damper on things before they even get going. Don’t rush into a relationship with someone you don’t know that well. Even if the two of you are a good match, you need that early dating stage to properly build the knowledge and trust that is the foundation of love. Take things slow. Your relationship will be stronger for it.”

Never say, “I’m too old for _______.”
“A common phrase amongst older adults is, I’m too old to do/try that, but that couldn’t be further from the truth,” says Linden. “Skydiving, traveling to a new country, and attending rock concerts don’t have to stop once you reach a certain age. Trying something new will always be intimidating at first, but it can also make for some of the best experiences.” 

Never turn a first meeting or a date into an interview.
“Sometimes, over-50 daters tend to focus too much on inappropriate details. They’re in a hurry to begin a relationship and feel that interviewing will speed up the process,” says Goldberg. “Don’t quiz anyone on their divorce. Don’t quiz them on finances either. You may think you’re being subtle, but it won’t work.” 

Never recreate past relationships.
“As someone dating in your 50s, chances are you have a few relationships under your belt. These relationships are an important part of your story but they’re in the past,” says North. “Resist the urge to compare new people to those you dated before. The best thing about continuing to date is to discover new and different ways to be with people you care about.” 

Never leave it open-ended.
The great thing about having plenty of life experience is you know what you want without even having to put it into words.

“But make sure your lover feels the same way,” says North. “Don’t let your relationship be open-ended. You may assume they want the same things you do but this may not be the case.”

This is especially true with dating in middle age as you both have spent a lifetime establishing what a relationship means to you. Before you get into a situation that you’re not expecting, define what you’re looking for in the relationship and have the conversation.

Never let others tell you how to dress.
Have you ever heard, “Women over 50 shouldn’t wear ______,” or “If a man wears a sweater vest, he probably owns more than 5 cats.” We suggest taking those arbitrary rules and tossing them aside. Wear whatever makes you feel comfortable.

“If wearing a sleeveless dress makes you feel confident and sexy, wear it. If you want to wear those sweater vests, go for it. You’ve earned the right to wear what you want, whenever you want,” says Linden.  

Never spend more than a few minutes talking about your family.
“Too many over-50 daters dwell on their grandchildren on a first meeting. Seriously, you need to establish a connection based on mutual values and passions that can be shared,” says Goldberg. “There’s plenty of time for the joy of family later, when you’re dating.”

Never talk about your health problems or your impending surgery.
Talk about a date ender… This means no talking about that prostate, varicose veins or, well, you get the point.  

“Keep it light. Yes, you may have challenges health-wise, and who doesn’t? Save it for later, when you can both share and certainly when you know each other better,” says Goldberg.

Dating after 50 isn’t all that different than when you were younger, but (and here’s the thing) you’re different. Make sure how you approach dating in the way that makes sense for you and what you want from your relationships. And don’t let a little thing like age hold you back.

Ashley Papa

Writer and Author

Ashley is a relationship writer and author of her first novel “Vixen Investigations: The Mayoral Affairs“. She writes about it all: sex, love, dating, marriage, and “crimes of the heart”.

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