Midlife Dating

If you find yourself in the unfortunate situation of dating later in life, realize that the more you know and love yourself, the more fun dating can be.

Learning to love yourself makes dating a lot more enjoyable.

Midlife Dating. I mean is dating at any age ever easy? In high school and college, you are young and so self-conscious and you don’t know who you really are so you’re trying to be whatever you think your date is looking for. Then you get a little older and if you’re like me, the next time you’re dating, it’s after a divorce and you know more about who you are and what you do and do not want in a partner. I remember going on some wonderful dates with interesting men, having thought-provoking conversations, and then never hearing from them again. WTF. There were a few post-mortem inquests into my actions. 

Should I not have said that? 

Did he not like this? 

Did that bit about my past turn him off? 

I started to second guess being my authentic self and sharing my life up to that point. I did that exactly twice and then I decided, nope that’s bullshit. I’m going to be me and share what my life has been and what I hope for it to be in the future and if that scares you off, you are definitely not the man for me. I also resolved to take the urgency out of dating. Maybe I will meet the guy of my dreams but in the meantime, I’m going to enjoy getting to know other human beings and connecting with them on some level and leave it at that. We both love to travel, amazing where is your favorite place to go? We both had parents in the military, crazy. How did you deal with moving every few years? Do you hate cats? Check, please. If they call, great if they don’t that’s great too. I quit taking it so personally and I started to have a little more fun with it. 

Dating SHOULD be fun. Why do we make it so uncomfortable? I have heard horror stories from my more prolific dating friends. One woman I know who is rather tall met a petite man for a date and while they sat at the bar and chatted, he confessed he wanted to climb her like a spider monkey, on the first date. Diminutive in stature, and ludicrous in personality do not a Prince Charming make. Even the bartender was dumbfounded and you know they hear some colorful first date conversations. After I moved to New York I didn’t really date much. At that point, I was in my 40s and most men my age have wives and children. If they don’t, they are divorced and not usually looking for an age-appropriate partner. Stereotypical but true. If they’ve never been married and haven’t had major therapy there is no question as to why I wasn’t interested. Not that everyone has to get married but most people want to find a partner to share life with. Humans are social creatures and we thrive in a community. If you’re still single and hanging out with your college friends as your life companions in your 40’s you might want to address your life choices. Judgy? Maybe, but I was married to a man-child the first go around and I had no desire to fill my vacant relationship spot with another. 

I did “date” a man right before I moved to New York. I use that term loosely in this instance as we never really defined it as a relationship. I knew him through work and while it seemed smart to keep it low-key while we were at work, I discovered he was restrained all time, never actually wanting to make any effort for it to be a relationship. We would meet up at a little out-of-the-way dive bar with a gravely voiced proprietress slinging stiff vodka sodas and emceeing the karaoke on Wednesday nights. It was fun and carefree and we would hypothesize about life and the paths we had both taken that got us to where we were. He was creative and mysterious and had the bad boy thing I was always so enamored with. It was never to my benefit mind you, but it drew me like a moth to a flame every time. 

About 6 months before I got on a one-way flight to New York, his romantic tactics shifted. He started asking me out on actual dates. We attended the Newport Beach Film Festival, hand in hand. He invited me to Palm Springs with two other couples for a weekend away. We made dinners at his place and he asked me to come with him to pick out furniture when he bought a condo, asking for my opinion as if it mattered to the outcome. One night in late May he asked me half-jokingly when I was moving to New York, as I had pontificated about it for almost three years. “Well, the loose plan is July 4th” I replied. I don’t think he believed me but he didn’t broach the subject of my staying. I really wanted him to ask me to stay. I was falling for him hard and I could see a future together. Were there red flags I was ignoring? Completely. Did I care? Not at that moment. I just for once wanted someone to pick me. I could envision us building a life together. He was creative and smart and edgy and playful. But he never said “don’t go,” and in hindsight, it was a blessing that he didn’t because New York actually ended up being the best thing that ever happened to me, not him. Right before I moved he shared I wasn’t the only woman getting his attention. I swear that devil tattooed on his arm winked at me when he said he’d found someone else. Curious, as I wasn’t aware he was looking. We both moved on. I fell in love with New York and he fell in love with a 25-year-old. Of course, he did. 

Once I moved, I dove precipitously into a whirlwind romance the likes of which I will never recover from. New York had my whole heart and I did not need a man to amuse, entertain, fascinate, thrill, or charm me. The City did that every day and didn’t ask me to pick up their dirty socks. While there were events I would have enjoyed sharing with a partner, I never felt incomplete exploring solo. I’ve always tried to relish my singlehood knowing that when it would inevitably end I would miss it. I dabbled with a few men from my past who lived in other cities and delighted in the attention and the distance. A couple of them did make the effort to come to New York for a visit and then promptly returned home I think to both our inclination. We all knew I wasn’t moving to their City and they weren’t moving to mine and the dalliances all came to their natural culmination. 

I found myself still single at the beginning of 43. And then another blast from the past out-of-towner resurfaced. B’s relationship had run its course and waking up after a regretful late-night Facebook message that I assumed would never be returned, I got an email from him. I sat there with my mouth gaping open reading words I never thought I would hear from him.

“step-1.
Got your FB message. And, have finally realized something. After all these years, not sure how to re-approach, but nonetheless have come to definitively realize, that I can’t stop thinking about you.

I can try, but it doesn’t stop. Would love to have you in my arms.

B”

Well, this is an interesting turn of events. I rubbed my eyes and read it a few more times to make sure I wasn’t still asleep. But even in my somnolent haze, deep down I knew it wasn’t going to work. I was never moving back to Orange County and with his kids firmly ensconced in their lives, I knew he wasn’t moving to New York. But I won’t lie and say that message didn’t feel damn good and validate all of the things I knew to be true. 

I am worth the effort.

You made a huge mistake letting me go. 

I am an amazing woman.

Some guy will be so lucky to have me.

There was a short-lived reunion a few weeks later in Orange County that was familiar and comfortable and fun. There were dinners, drinks, and relaxed conversations. A reacquainting so to speak. He was affectionate and gentlemanly, dropping me off at the airport in Long Beach and sending flirty texts while I waited for my flight. The next day, came the reality check that things were not quite wrapped up emotionally for him and he was having buyer’s remorse for opening a door he probably should have kept closed. While I respected him for actually calling me to say the words aloud this time as opposed to ghosting me, I’m pretty sure my eyes rolled so far back in my head as to see my brain as I nodded silently on my end of the phone. Of course, he needed time to “sort through his feelings” and “he wasn’t over his ex yet.” I knew that night that my heart had healed from a version of a future I thought I wanted and it no longer mattered if he was interested in pursuing a relationship or not. I was no longer interested. That door was closed and I actually hoped he would be happy.

When they say things happen for a reason, it’s not just because it’s a cliche. A few months after I closed the door on a relationship I thought was right for me, another door opened that was actually right for me. With all of my past “what if’s” wrapped up with a neat little ribbon, I was open to the man who would become my husband. Dating is much more fun when both parties are invested and know their worth. You can be open and honest and share the path your life has taken, with all of its hilarity and heartache. That’s when dating does get fun.