21st Century Dating for Baby Boomers: Tips on dating now vs. then

Posted by in dating after divorce, single women over 40 | 2 comments

How is dating different in our 50’s & 60s than it was when we were in our 20’s?

The most obvious difference in dating today is the advent of online dating, in my opinion a must for anyone dating. Period. If you had to rely on being fixed up by friends, you would probably have very few (if any) dates.
In the old days, there were dating ads that people could place in newspapers and magazines. “SWF seeking SWM for dating/marriage”. Many people met their spouses that way. Dating online opens the possibility of meeting someone more like you, and easily connects you to people all over the world. It expands the dating world and brings people together who might never have met. Sure, it can feel creepy and you may not be so comfortable putting yourself out into the world wide web, but online dating has become one of the top ways to meet your spouse. If you need help, click here for my online dating profile essay packages. I offer several ways to make it easier for you.
Another difference is the level of self-knowing and confidence that comes (hopefully) with the wisdom of aging. Being able to communicate more clearly – knowing who you are and what you need – all make for better relationships.
When does a relationship move from casual to serious?

I think that middle-aged people are usually more clear about what they want/who they click with, so if there is chemistry and you share common goals/values, relationships can get serious pretty quickly. Conversely, if the key elements are missing, they often don’t progress past a first date. Next!
How do you deal with adult children?

I believe in introducing your girlfriend/boyfriend only when you are certain that it’s a serious relationship. No matter how old your kids are, they usually don’t want to meet your boyfriend/girlfriend right away. It can make them very uncomfortable. You can always check in with them and see when they are ready. Of course, it depends on your personal situation, so if a person is widowed or divorced for a long time, the kids may welcome a partner in your life.
I hope you find these tips to be helpful. As always, I welcome your ideas. Please share your thoughts and comments below. And happy dating!



  1. Thanks Sandy for such a useful guide to the potentially touchy subject of bouncing back from loss and entering the dating game as a boomer. I agree with your breakdown of the differences and changes in the dating game, but I would also add, that truly deep down, the whole purpose of dating hasn’t changed one bit. While some of the technology may have been updated, it’s still the main core goal of meeting and getting to know someone, making a genuine connection, and finding someone to spend the rest of your life with!

  2. Hi Donna,

    Thanks for adding your words of wisdom to my post. Yes, I agree, dating is still pretty much the same as it was when we were younger, but I know that as my children leave home and I become an empty-nester, the intent is a little different. This time, it’s about finding someone to enjoy spending time with. Way back in my twenties, my goals included finding a potentially good father, and a provider who could support me. I can now support myself and my kids already have a dad. This time, it’s for a deep loving relationship, pure and simple, but not so easy to find!

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