Dating in My 40’s — #24 Why Do I Put Myself Out There?

Jill Ekard
P.S. I Love You
Published in
9 min readFeb 21, 2019
Photo by manu mangalassery from Pexels

Being back on the dating sites after four months of reprieve was not on the top of my list of fun things to do. But I was single again and still wanting companionship with the hope of a relationship, so recently I went back onto OKC and Bumble to see what was out there.

Serial Monogamy Dating

When I go on a date and I like someone or we click, I prefer to pursue that one person until we both decide whether or not there is mutual, continued interest. When I met this new guy on OKC… let’s call him Paul… I was excited to see if there was chemistry. However, I didn’t put a lot of hope into it since it was only the second guy I went out with since my last breakup.

The First Date

Paul met me for a drink and I was quietly excited to see that I found him attractive in person. I tried to play it cool of course, but it was even more exciting to learn that he is successful in his career, highly intelligent and as normal as he could get, at least from what I could tell during our four-hour first date.

We both hit it off nicely and it was clear we were both interested in seeing each other again. He didn’t waste any time asking me out again and offered to see me two nights later if I was free. During our conversation on the first date, he told me that he knew exactly what he wanted in a woman. He even admitted that after two dates usually he could tell if the relationship is worth pursuing or not.

I know I’m successful, fun, highly intelligent, generous and a lot more great things that make me a catch for a man. However, I seem to have trouble finding a man that recognizes how worthy these qualities are. So when Paul seemed so obviously impressed with not only my looks but all these other qualities that make me special, I was really encouraged. I told myself when starting back on the dating sites that I was going to take the next dating experience slow and not let myself get connected to a guy too quickly. Yeah, right.

The Second Date

On the second date, Paul asked me over to his place for a couple of hours. We had really deep conversations about life, about our goals, our desires, our past, and our relationship experiences. It was something new to me to have such deep conversations and share such private emotions so soon. I liked it though. I felt like I was connecting with him on an intellectual level and that was comforting. He asked me out again for the next night which happened to be Valentine’s Day.

Okay, ya’ll, I’ll admit that I was not happy this month about the prospect of not having a boyfriend or a date on V-day. To me this screamed “LOSER”! Rationally I know it’s no big deal, but emotionally I was so hoping to have a date.

The Third Date

On Valentine’s Day, Paul and I picked up tacos for dinner and brought them to a local brewery. We ate, had a couple beers and talked for hours. He didn’t bring me a rose or make it the most romantic date ever. But I didn’t need that. For once I was connecting with a man and it seemed like our values were lining up well. We both expressed to each other that our instincts in dating often led us to date one person at a time until we saw the relationship to conclusion — either a LTR or going our separate ways. We both clearly liked each other a lot by this third date and we wanted to see where it would lead. We, of course, weren’t talking about dating exclusively. But with so much opening up of true feelings and goals we both knew that if we were going to date each other and get to know each other, we each would not pursue anyone else. I was on cloud 9 by the end of the week thinking how cool it was that I met someone so awesome with so little searching. He had only been single a couple weeks after just having broken up with the woman he had been dating for 5 weeks.

As far as I could tell, Paul had dated a lot since his separation a year ago. He had a few short term relationships and also went on dates where he made it through 2, 3, or 4 dates before one of them decided it wasn’t going to work. By all accounts it felt to me like the attention he was showering on me was a bit unusual for him.

The Fourth Date

I took a chance and asked him if he would like to go walking on the local bike trails a few days later. He said he would love to, so we went that Sunday morning on a 5-mile walk. He said something on that walk that stuck with me days later. I asked him if he ever felt like he was in love since his marriage ended a year ago. He said he thought maybe he was once in love but it was very early on after he separated from his wife. He had been very hurt because his wife ended the marriage. He was extremely vulnerable. He met this woman that he started dating and I could tell he adored her by the way he described their relationship. He told me that he felt like she was the one for him. But he was still hurting after his marriage and she must have recognized that because she broke up with him saying that he needed to heal and discover himself before she could possibly be in a long term relationship with him. He told me that when they were together the words I love you slipped out by accident once. He knows now that it was probably not love, but he was feeling it at the time. He was almost embarrassed that he said it out loud to her. It occurred to me after our walk that he’s not over this woman completely and I wondered if he holds out hope that she would take him back some day. I almost asked him if he’s still in touch with her and if she has met someone else since being with him. But I didn’t.

Before I left him after our walk, he asked me to go paddle boarding with him the next weekend. We made plans to do that. Then the next day he texted me and asked me to come have dinner with him one evening over the same weekend. We had two dates lined up and I was looking forward to them. He texted me with interest each day during the week.

The End

Then by mid-week, I got a text from him in the middle of my day while I was at work. He said he’s sorry to drop this on me but that a woman he used to date contacted him the day before. I thought I was reading the text wrong because it said he had so many thoughts of what-ifs when it came to her and he couldn’t let this chance pass him by. He didn’t even come right out and say I’m going to date her and therefore I don’t want to date you anymore. I mean, I could read between the lines, but like an idiot, I actually wrote back “So does this mean you don’t want to go out with me anymore?” I know… I sounded like a teenager. I just really couldn’t believe that someone could act that interested in me, being the one to pursue me so eagerly, and then a couple days later be okay with never seeing me again.

Now I know what you are thinking: I had only known him a week. Right. So no big deal, he picks an old girlfriend over me. Completely understandable and it should be easy to just move forward and not be affected by his response. Wrong. I put myself out there. I let myself be vulnerable to him. I opened up to him and I started to like him. I started to think about him in that LTR role to see if it would fit. You know what I mean!

You ask yourself, could I see myself going on a vacation with him? Could I imagine what a fight with him would be like? Could I envision living with this person? Could I conceive of meeting each other’s kids or friends or family? I know this seems silly to some people. But I have to be able to see someone I am dating fitting certain roles and having certain qualities and if I can’t envision it, I won’t want to date him long term. So I let myself picture these things and the initial assessment told me that he fit what I would want or could want. I knew it would take months more to really get to know him and assess our compatibility. But I was already thinking about what our relationship would be like. Suddenly, though, that was gone with a snap of my fingers… or more accurately the ding of his text message.

Aftermath

It’s six hours since he sent me this text. I’m fine now and I’ve already put the idea of him behind me. I’m embarrassed to say I shed a few tears on the way home from work. I felt like I lost something that “could have been”. It had definite potential. I also felt a bit rejected. It’s hard not to feel like second best when someone drops you faster than light speed when an old girlfriend contacts him. I know I’m worth a lot more than being someone’s second choice. I told him that in my response text. I might have been a bit snarky about it. I told him that when she decides to drop him again, don’t contact me. I don’t do second best. He was apologetic and sympathetic back to me so I know he had a hard time cutting it off like that so abruptly. At least he’s human and a good guy deep down even though I wanted to call him a jerk to his face. I do wish him and this woman the best even though part of me hopes she dumps him within the next month so he realizes he was being stupid.

This whole experience in the last week made me think about how hard it is to put myself out there in the dating world. I am a very emotional, empathetic, and generous person. When I like someone I give a lot of myself, including my time, my emotions, and affection. So when I like someone and get to that really vulnerable place, I am at risk for getting hurt pretty badly if it doesn’t work out. It doesn’t matter if I date that person a week, a month or a year. When I put myself out there and make myself vulnerable, I can almost guarantee the hurt is coming. I’ve even broken up with someone because it wasn’t working and I felt a lot of hurt afterward.

So is it worth it? I really don’t know anymore. I am not sure if at 47 years old it is possible to find someone that matches my values, needs, goals and desires. And then if he does, will I even be attracted to him and feel that spark? Will he feel all that for me? How do we find love again when we are in our 40’s and set in our ways? Plus, we have the stresses of taking care of our kids, focusing on our careers, taking care of our homes, and finding time for family and friends. There’s barely any time for a relationship, even when I really like a guy. I’m going to sit on these feelings for a few days and explore what to do next. I have not really considered this since my divorce that maybe I would be better off on my own for a couple years. I mean, I still could meet the love of my life at age 50 right? Yikes. I don’t even want to think about it. I said to a friend tonight, “I almost wish I could go back to my 20s when I had no idea what I wanted in a man and I was completely naive that I could love the same man forever”.

If you are in your 40’s and are in the dating world right now I would love to hear in the comments how you are coping and what strategies you use in dating to be patient when trying to find “the one”.

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Jill Ekard
P.S. I Love You

Career woman, mom, book lover, movie buff, aspiring writer and seeker of Mr. Right. Don’t forget to stop and smell the roses!