Running with Scissors (Dating – Part 1)

I’m 53 years old and I have rejoined the dating pool.

While this might seem exciting to some, the reality is that dating as an over-50 woman, during a pandemic no less, is challenging – to say the least. Prior to splitting with my ex, the last time I had gone on a date was 1992 – nearly 30 years ago. And, while I consider myself a pretty progressive person and in touch with the latest trends, the marketplace for prospective men was outside of my scope of knowledge. I knew that 98% of my opportunities to meet men would come from dating apps (and, when COVID hit, that increased to a full 100%) but I did not understand a lot of the nuance of the online dating world. It was confounding to me how many of the profiles on the apps are fake and I needed to search the urban dictionary to understand some of the lingo:

DD Free? (Drug and disease free)

LTR? (Long-term relationship)

GGG (Good, giving, and game – in bed)

FWB? (Friends with benefits).

I was flabbergasted when learning how many middle-aged men want to be dominated or want to find women who are submissive. Wow! And, thrupples? Holy cow. It was an immersive learning process for me that did not come without its share of pitfalls. I learned how some guys just want to sext (yes, that is a modern-day version of phone sex) but never actually want to meet you. I had my share of ghosters (that was really a new one for me) – guys who either talk to you a bunch or even meet for a drink and then totally disappear without a word. That has probably been my biggest agitation and disappointment. If you have made it through 50 + years of life, you can do better than just disappear. It is not that hard to tell someone that you’re not interested. Needless to say, the learning curve was steep and I realized quickly that I was way out over my skis. It was going to take some time for me to get a handle on how to manage this process.

For years, long before I actually mustered up the courage to tell my ex I wanted a divorce, I had given a lot of thought to the characteristics I wanted in a partner. I used our couple’s counseling sessions to test if those traits could be manifested in my marriage but it was quickly evident that it wasn’t possible. If I wanted to experience a relationship with the type of partner I was seeking, it was going to have be with a different person than my ex.

To be clear, my ex-husband is not a bad guy. In many ways, he is a terrific guy. He was just no longer my guy. He has always been a devoted dad to our kids and has done his best to help them turn into the wonderful young men they are today. On my worst days, when I am feeling angry or frustrated, I remind myself that without my ex-husband there would never have been my children. And, in no universe would I ever want to rewrite that script. They are the best things that ever happened to me as I have shared in my journey of motherhood.

My ex and I did not have a “conventional” marriage. Our roles were less traditional with me traveling for work 40-50% of the time. I run a business and my time is very consumed with my work so, as a result, I did not spend much time taking on more traditional tasks like cooking meals for my family. I rarely stepped foot near the washer or dryer and only took on the role of resident clothes-folder when I was in between cities. My children were in no way neglected as I managed all my parental responsibilities from airports and hotel rooms and used my time at home to spend quality time with them. I sacrificed things like a social life so I could create some level of balance between my work and family. The net result of this lifestyle was that I became the primary breadwinner and left the more domestic responsibilities to my ex-husband. We never actually discussed this dynamic; it just sort of evolved organically. I’m not sure either one of us liked our respective roles but, as time progressed, we became more characterized by these roles and it was both damaging to and definitive of our relationship. I also had the opportunity and good fortune to escape a lot of the unhappiness I was experiencing at home by being away from home.

Once it became clear that divorce was imminent, my therapist and I worked together to help me identify the characteristics in a man that were to become my basic requirements. I wrote them down, looked at them regularly, and practically turned them into a mantra. I was meditating on these ideals and working towards manifesting the man I wanted. As my ex and I went through our ups and downs in the last year of my marriage, I tried to convince myself, in the good days, that he was beginning to check off my boxes. Ultimately, it was confirmed again and again that my desire to end my marriage was legitimate. As this process was unfolding, my therapist also encouraged me to start considering how I would get those boxes checked and my buckets filled. Everything I had read about divorce suggested that you wait a while before dating and figure out what you want. Article after article encouraged newly-split partners to “find themselves”. I discussed this with my therapist and we both came to the same conclusion: I had long ago found myself but then got lost inside my marriage. So, as soon as I came clean with my ex about my desire to split, my therapist encouraged me to dive into the deep end of the pool.

Say what?


I was terrified…but also a little excited. I never cheated on my husband but, many times over the years, fantasized about what it would be like to be able to go out on a date and experience all the excitement that comes along with it. I figured, now that I was on my way to being single, I could have some fun with this. And, I thought I had my shit together! I was attractive, had a good job, a great personality and was oozing with newfound confidence. How hard could it be for me to find a man to date?

Ha Ha

I did what I thought was the appropriate course of action. I created profiles on all the popular dating sites. I learned how to take flattering selfies (shoot from above), used my writing skills to create a compelling profile, and set out to find the man of my dreams.

Womp, womp.

Yea, it doesn’t work that way. I suppose, in every Pollyanna rom com where the way-too-gorgeous (think Julia Roberts or Julianne Moore) “older” woman is searching for her Prince Charming, some magical meet-cute happens and she bumps into him in a bookstore (think “When Harry Met Sally”). However, when you are middle-aged, have had no work done to reverse the hands of time (nope, not even a Botox injection), have had two pregnancies and two c-sections (and all the stretch marks, extra skin, and scars to prove it), and are perimenopausal, spending more time working than at the gym spinning, the search for a man to date becomes increasingly more challenging. The only thing that buoyed me was that my requirements didn’t align with many of the complex checklists other women apparently compiled. My superficial requirements (tall, facial hair, nice smile) set a relatively low bar and I typically have a specific type. He is definitely not the guy who spends countless hours doing Cross-Fit. I am more attracted to big teddy bears who likely have more hair on their chest than on their heads, have sweet smiles, and, generally, wear glasses. These were the same guys who, in college, wouldn’t give me the time of day because they were cute Jewish guys who weren’t going to put any effort into a half-Jewish girl who never saw the inside of a synagogue. I was not marriage material for them. These guys, now middle-aged and divorced, were still my type, albeit beefier and with hair that had shifted off their heads. It remained to be seen if I was now an acceptable candidate. The primary challenge I was regularly encountering was that there was little inventory of men who met my 6’ minimum (for which I was shamed despite the fact that most guys wouldn’t even consider dating a women larger than a size 4 – to them, curvy meant Barbie Doll or Kim Khardashian. Um, no). Most of the guys I came across were either my height (5’8”) or shorter and this was an absolute dealbreaker for me. I could sacrifice the hair, the glasses, the sarcastic wit but I would not date a man shorter than me. My only other requirement (and we were working on the honor system here) was that the guys knew how to kiss a woman properly. Regularly, back in my younger dating days and, even with my ex-husband, I had to teach men to slow the hell down. Kissing is a marathon, not a sprint. I get that younger guys are focused on kissing as a way to get into a girl’s pants but, at our age, kissing is often the appetizer, the entree and the dessert.

I figured my simple taste and needs would have been beneficial to me considering that most women are way more superficial than just having a height requirement. Men practically needed to come to their first dates with income verifications, five years of tax returns, the deed to their vacation home and a deposit for the eventual 3-caret diamond engagement ring. I just wanted to be able to have to stand on my tippy toes when it came time to kiss goodnight. I figured I had to have some advantage here.

Sure enough, I started getting responses to my notes. I definitely had some of my better photos posted and I knew I was capable of writing a good introductory message. I can be funny as hell and I left no joke unturned if I thought it was going to lure someone into my web. Use what you’ve got, ladies! Within a few weeks, I had enough guys on the roster that one of my close friends suggested I create a spreadsheet to keep track.

Since I teach people how to communicate for a living, I was pretty confident that I could tackle the next step in the courtship journey – the phone call. My phone skills were honed. Yes, I give good phone. I can pretty much carry on a conversation with anyone. 30 years prior, when I was a young 20-something in the dating world, I was terribly shy and introverted and definitely did not know how to flirt or use my femininity to attract a guy but now, armed with self-assurance and wisdom, I felt pretty comfortable turning on my charm. And charm I did! I quickly landed a few dates and, before I knew it, I was on a mission to kiss as many toads as necessary to find my prince. Plus, I wanted to learn what chemistry felt like.

OK, if I am being honest, I kinda loved the making-out part. I really enjoyed the idea of just kissing guys like I was a 16 year-old at a high school party. It felt so exhilarating to initiate the kissing and try out my skills with different guys. However, the novelty quickly faded as I remembered that the best kissing is with a guy that you knew, were highly attracted to on an emotional level, and that would lead to something more. The random make-outs in my car or in a parking lot or in a dark restaurant were fun for a bit but then I began craving more. I wanted to date someone more regularly. That was a bit more complicated because, to find someone with staying power, I had to be more discerning and needed to get back to my list of characteristics.

I whittled down my list of candidates and my spreadsheet got smaller and smaller. The first guy I dated was someone I had initially passed up because I thought I had met another more eligible beau. After that guy ghosted me, I licked my wounds and reached back out to the nice guy I blew off. He generously invited me on another date and we began seeing each other. It was fun and I knew, quite immediately, that he would be the one with whom I would lose my divorce virginity. And I did! It was surprisingly way easier than I thought it would be. In fact, I was shocked at how easy it was. Of course, I was grateful that he kept the lights dimmed so as not to showcase any of my unflattering parts. Happily, I was remarkably comfortable and my middle-aged confidence led the way. I was having empowered, perimenopausal sex! Holy crap! And I was loving it! I called my best friend on my way home from my first encounter and shrieked with joy. I knew the likelihood of this guy being a long-lasting partner was pretty slim but we had enough rapport and attraction to help me get back on the horse. We had fun sex, ate some meals together, chatted on the phone (I learned all about phone sex) and it was blissful. Until it was over. We sort of drifted apart and then I learned that he was seeing someone the whole time we were together.


So, this is a thing. I had no idea about this. I assumed that if we were sleeping together, we were only sleeping with each other. And, quite frankly, at our age, I didn’t understand how you could possibly juggle more than one sex partner. I mean, between work and kids, who the hell had the time to sleep with multiple people at once? And, how do you keep that stuff straight? It was a bit of a blow to what I believed to be a very healthy ego and I decided no more sex until I was certain I was dating someone who had the potential to be serious.

Back to the online dating and the spreadsheet and the one-off encounters and it was starting to get old fast.

It was now 2020 and some of you may recall that we started out the year feeling optimistic about the future. I had recovered from some back surgery in the fall and was feeling strong and hopeful. My business was booming and I was traveling all over the place. One of my handsome male colleagues assured me that, above all else, my booming confidence and sparkling wit would land me a great guy. If he thought I had a chance, that was a strong vote of confidence. Nonetheless, my hopes were dwindling and looming over our heads was this coronavirus thing happening in Asia and Europe. I listened half-heartedly to the news and, occasionally, when walking through an airport, I considered that I should probably not touch too many things, carry some hand sanitizer and be sure to steer clear of anyone sneezing or coughing.

There is a distinctive pattern to how foolish and naive I can be at times. And, well, you know the rest of how that whole pandemic thing went. My life, however, took a sharp left turn just as the virus was making its way into the United States.

Right before the quarantine began, I met a guy on We clicked right away and we were both anxious to meet before we were going to have to stay put for an extended period of time. We agreed that if we were to invest the energy in getting to know each other from a distance, we should meet first and make sure there was chemistry.

There was.

There was a lot of chemistry.

We had a first date, confirmed that we were attracted to one another and went our separate ways, unsure of when we might be able to see each other again. We texted and talked daily. During the next month or so, we met regularly for outdoor dates and, as time progressed, the relationship became more intimate. It felt like the relationship was progressing. I could see myself developing real feelings for him and he was sending me all the signals that he felt the same. Our relationship made me very happy and was a wonderful distraction from the malaise that was hanging over our heads from the pandemic. Things were stressful outside of our little bubble and we both balanced our anxieties about our work and the health of our loved ones with the enjoyment of our burgeoning relationship.

One big lesson for me from this relationship is that sometimes things are not as they seem. Despite having dated a number of men prior to meeting this guy, I was not savvy enough to read the cues. I allowed myself to believe that the relationship was heading in a direction that, perhaps, was not the experience for both of us. About three months into the relationship, I decided to disable my account. My focus was on this relationship and I had no interest in searching for other men during that time. When I went on the app, I noticed that my new beau was online. My stomach twisted in knots. What could this mean? Was this normal? Perhaps he was doing the same as me. I checked back a few hours later and saw that he was offline. The next morning I checked again and he was online. I was hurt and confused but, given my relative inexperience with online dating, I didn’t want to jump to conclusions. He called me that morning to say hi and everything seemed lovely and fine so I decided that I was overreacting and things were fine. As the day progressed, my confidence was wavering and I was getting more anxious by the hour. This was the same guy who said he was a “one woman at a time” kind of guy. How could he be seeking out someone else when we were sleeping together? I felt deflated. And, I felt stupid. He had been divorced for many years and I was still very new to the process. I naively expected that, even though we had not discussed exclusivity, that I could take him for his word or, at least, he would tell me if he was not feeling good about the direction we were heading. I was, by no means, looking for any kind of commitment but it did not seem unreasonable to expect a bit more transparency given our situation. And, all of this, I soon became acutely aware, we’re gross overexpectations on my part. I learned the hard way that dating after divorce comes with a whole different playbook. It’s great that we are not looking for mates with whom to procreate and that we know ourselves so much better now so we can better scrutinize our dates. However, men and women have very different approaches to later-in-life dating and the language and expectations differ. Without a good deal of experience, you need to carefully walk through the minefield of dating to ensure you do not blow up.

I blew up.

Later that day I called him and explained that I had mistakenly not asked him about sleeping with other people while we were dating. I made it clear to him that having multiple sex partners at once was not going to work for me. He didn’t respond well and shared that my comments were reinforcing his existing concerns that I was not ready for a relationship given that my marriage had ended so recently. I was taken aback by his response. Yet, my general philosophy when two people have such strong counter perspectives is to acknowledge and respect the other person’s point of view and also attest to my differing viewpoint. This was not well-received and I could hear from his voice that my new relationship was in peril. I wanted to shove all the words back down my throat, feeling like I had overestimated our closeness and my ability to communicate with him in a more intimate way. In hindsight, of course, I recognize that I didn’t do anything wrong. If a guy is sleeping with you and wants to have a relationship with you, his reaction to that type of question would certainly not be to tell me that I am not ready for a relationship. In fact, it was a giant red flag that it took me a while to see. The next morning, as I was about to text him to laugh off the previous day’s conversation, I received a breakup text from him. Yes, that’s right – A TEXT MESSAGE.

I was heartbroken. I hadn’t seen this coming and realized that the experience I was having with him was significantly different from what he felt. This crushed my confidence and gave me an important yet undesired education on dating. Finding a good guy is more like finding a needle in a haystack. It’s important to understand that men who have been through marriage and divorce are saddled with baggage no matter how much they claim to be traveling light. Men are foreign objects that need to be carefully studied and evaluated. No matter how much chemistry exists, it is not a predictor of whether or not you can sustain a relationship. In fact, sometimes the chemistry burns out so fast and there is nothing beneath to support it. With most of the guys I have dated, there was an abundance of chemistry, yet none have catapulted into a full-blown relationship.

My journey is just beginning and I am optimistic that there is someone out there with my name already tattooed on their heart. Since then, I have met other men albeit none who have checked my boxes or been a good match. So, I am using these opportunities to hone my skills and learn to identify the red flags much more quickly. I am in no hurry to meet someone and, truthfully, I am happy just having fun and meeting interesting people. After all, that is all that matters these days. These are tenuous times and I am still eating from the buffet. Eventually I will zero in on what tastes really good.

For now, I shall put the scissors away and walk slowly.

One thought on “Running with Scissors (Dating – Part 1)

Add yours

  1. Welcome to the world of online dating- it’s kinda fun and it kinda sucks too! I’ve written a bunch of posts about my experiences too; it all has to be taken with a pinch of salt, and the best advice I can give is to imagine yourself as the jewel on top of the mountain, and make them work to get to you! I’m 54, and have been doing it on and off for the last 10 years… good luck, G in Australia 🙂


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Website Powered by

Up ↑

%d bloggers like this: