5 Lessons Learned From Dating in My 40s

Couple on Boardwalk
Couple on Boardwalk

Met him at 18. Married at 21. Divorced a month shy of my 40th birthday. Suddenly I was single again, for the first time in 21 years. Gulp.

I took time to heal -- probably not enough time, truth be told -- and then I decided to try my luck in the dating world. What I didn't realize was just how much dating had changed since I was 18. When I last dated, cell phones were a rarity that were installed into the floorboard of your car and texting didn't exist; neither did Facebook, nor online dating sites, for that matter. If you wanted to ask someone out, you called them on the phone; yet at age 40, I no longer had a landline.

I know I'm not alone here. I've spoken on enough telesummits about finding love later in life to be able to put the high divorce rate = people are dating at all ages equation together in my head. Yet, actually getting out there and meeting people in my 40s often feels like I'm visiting another planet. So, I did what any good researcher-by-training would do: I studied my demographic, experimented (a.k.a. went on dates), and analyzed my results. Here's what I learned:

1. Make sure you're ready. Watching my friends interact on online dating sites made me realize that dating can become a full-time job, if you let it. When friends encouraged me to try online dating, my first response was, "I don't have that kind of time." That was my excuse for months, until a friend finally called me on it. It wasn't that I didn't have time to date; the reality was I was scared and wasn't really sure I was ready to enter the dating world. There's a right place and a right time for everything. Make sure it's yours.

2. Trust your intuition. I've had a few first dates that left me wanting to run for the hills. Yet, sometimes I ignored the red flags and went on second and third dates. Ladies -- there's a reason we have that thing called women's intuition. If you see a red flag, do not ignore it. Figure out what it is and why it exists. Then decide if you want to entertain another date with someone.

3. Figure out what you want and what you don't. My first relationship post-divorce was with a man who found me on Facebook. He asked me out for a month before I agreed to meet him for tea, but because we shared a number of mutual friends who assured me he wasn't a serial killer, I finally relented. I learned a lot about myself from the relationship that ensued; namely, that I really wasn't ready to be in another relationship only 10 months after my divorce. It was simply too soon. I needed more time to heal and process. Although the relationship I had with Facebook Man ended after only six months, he was a great mirror for me and helped me heal from my divorce. Most importantly, I learned what I wanted (and what I didn't). A few months after that relationship ended, I made a list of what I wanted in a partner. Every time I went on a date, I found myself adding to that list. It's now three pages long! But that list has saved me. After meeting a new man, I consult my list and see how he fits. Does he have the qualities I'm truly looking for? Can I be the woman I want to be when I'm with him? My list helps me stay grounded through the initial excitement that comes with first dates; it helps me discern if a particular person is a good fit for me. Maybe lists aren't your thing -- and that's fine -- but I do think it's important to figure out what you really want in a partner (not hair color, eye color, etc., but the qualities that are important to you). Trust me on this. There are a lot of fish in the sea; don't settle for one who won't help you be the best version of you.

4. Own your worth. I have a lot of strong female friends, women who run boardrooms and manage household affairs like nobody's business; yet, get these same women into the dating scene and they forget who they are. Their "not enoughness" issues come forward, and they suddenly think they'll never do any better than the man who [insert problem: is an addict, is looking for a sugar momma, treats her like crap, etc.]. I know because I was one of those women before I made my list (see Lesson 3). Ladies, you deserve a partner who treats you like a queen. Do not settle for less. Own. Your. Worth. You will never find a partner who treats you like you want to be treated until you begin to treat yourself that way. If that means taking time off to heal your "not enoughness" issues before getting back on the dating scene, then do it. Your happiness is too important to let this slide.

5. Be open. Sometimes true love comes via an online dating site; sometimes it comes from a chance meeting at a coffee shop; sometimes it happens when you're out dancing with your friends at a gay bar, trying to avoid men for a night. Once you've figured out what you want and owned your worth, put it out there and let the universe take over. But be open to receiving it when it comes -- even if he's not quite what you imagined, or you met under "interesting" circumstances, like at your uncle's funeral. As long as you've owned your worth and gotten crystal clear on what you want, it will happen. Let it.

Happy dating! Let me know how it goes in the comments below.