Dating and seeking big love at 50+, or any age, is a lot of things. There are those who characterize it, and I quote, “a drag,” “scary,” “an exercise in futility,” ” a time suck,” and “frustrating.”

Not gonna lie … sometimes it does feel that way. However, since I’m essentially an optimist — I’m all about shining, remember? — I prefer to think of the love-finding process as fun, entertaining, empowering and yes, a source of personal growth and insight. And who doesn’t want more of that?

  1. Dating gets you out of your comfort zone, bumps you into your fears, and gives you the opportunity to work through them. Whether it’s being seen and “out there” posting a dating profile, clearly articulating a vision for the kind of love you want, or meeting a new person (never mind flirting, having sex and starting a relationship, perhaps after a long dry spell), the process can bring you up close and personal to your stuff. And, if you truly want to achieve the object of your desire, you eventually push through the resistance and make progress. Daunting and thrilling!
  2. It’s a great way to practice the concept of not taking anything personally. Easier said than done, right? It really is a key to overall happiness in this life. As you communicate, date and relate with men — especially in the early stages — some behaviors may surprise you (ghosting, anyone?). Little, if any of it, has to do with you as a person. At that point they don’t even know you!
  3. You gain clarity on what’s really important to you. As you chat online, meet people organically and go out on dates, your perception of what’s truly important may shift. It’s easy to get hung up on superficials like height, looks, job status, etc. Or to put too much emphasis on hot chemistry from the first date. While it’s great to have standards and preferences, sometimes a focus on these can be an excuse to not give a man who might be just right for you a chance.
  4. You cultivate your superpowers of discernment. A big secret to a fun dating life and finding real love is developing a good “picker:” the ability to suss out quality men from the flood of candidates online and in real life. How? By tuning in to what’s really important, getting a sense of who’s real and who’s, um, less real, reading between the lines, and paying attention to actions as well as words. I credit this with my overall positive dating experiences and very few “disasters.”
  5. You learn a lot from people you might have never met. If, like me, you’re open-minded and a good listener, you can have a delightful experience during a half-hour coffee date with someone you’ll never see again. If you’ve chosen your date wisely (see above), even if there’s not a connection for further contact, you’ll encounter interesting, smart people doing cool things with much to share … and so will they!


As with so many things in life, it all depends on how you frame it. As we relate to others in new ways, we learn so much about ourselves.

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