Adventures in Dating After Forty

I had a date last night. I know. It is hard to believe. I am pretty sure I just saw a pig fly by my window but it really did happen. To be completely honest, it was my first time dating since turning forty. This means it has been a couple of years since I have gone out on a date. Would dating after turning forty be better than dating in my thirties?

I was about to find out.

Dating After Forty

Some Backstory

The guy and I were matched a couple of weeks ago on Coffee Meets Bagel, one of the many, many date apps out there. We chatted through the app for a few days and then texted back and forth before finally deciding to meet. We agree to meet after work last night at The Marq, a bar in the loop.

Going into the date, I knew we had chatted in the past. He mentioned it to me while we were texting back and forth and I vaguely remembered discussing Hawaii with him. What I DIDN’T remember what that we had actually gone out a couple of times before. Um, oops! Total fail on my part and quite awkward but in my defense, he has a beard now so he looks very different.

It turns out that our REAL first date was on December 20, 2017. I know the date because it was the night before my birthday two years ago. So it seems that dating after forty is a whole lot like dating in my thirties…even the same guys are here! Ha!

The Actual Date

We started talking and catching up. I remembered him and the dates we went on after he reminded me so it was more of picking back up the conversation. We talked for a while – my travels, politics, Stella, his grandfather who passed away a couple of weeks ago, etc. It flowed well. About an hour into the date, I realized Iowa MBB was playing on one of the TVs by the bar. We decided to close our tab at the table we were sitting at and moved over to the bar so we could watch the game. This was a very sweet gesture by him and I appreciated it.

We had a good time watching the game. We bantered back and forth and laughed. He was a fun game watching companion.

While we were sitting at the bar, there was a woman eating sitting around the corner from us. She was eating dinner alone. Because I had had a couple of glasses of wine by this point, during a commercial break, I asked her if she was traveling for business. Seems odd but it was impromptu research  for a project I am working on (I will talk about that another time).

The answer was “no.”

Turns out, she works in the building and her husband was out of town so she was enjoying a nice dinner before going home. We started chatting and she referred to the guy as my husband. No, no. I instantly corrected her (side note: is checking for rings before asking something like that something only single people like me do?!). When we told her it was our first date after going out a couple of times two years ago, she said she was very surprised because we seemed totally in tune and comfortable with each other. She was guessing we had been together for a long time after listening to us talk.

We laughed it off. After she finished her dinner and paid her bill, she said goodbye and told us she hopes it works out because we were “two peas in a pod.”

There is a Catch

All of this seems really promising, right? I should be happy and optimistic. But there is an issue. Of course there is.

The main reason I did not pursue anything further with this guy two years ago was because he hadn’t been permanently employed for a while. I want the say it was over a year back then. He was doing some music lessons and house sitting to get by. He was also living in a “family owned” unit on the Northwest side of the city. I didn’t press what “family owned” means too hard although he said he lives alone so apparently he does not live with his parents.

Two years later, he is still doing temporary work and living in the same “family owned” unit.

I don’t want to date or have a long term relationship with someone who is not motivated or driven to find a long term job with benefits and who cannot support himself. If someone is unemployed for a short time or during a downturn in the economy? That is fine. I totally understand. But that is not what is going on here.

When I asked him about his employment situation last night, he mentioned that his current temporary position may turn into something permanent but he isn’t sure he will take it because he “sees through the corporate BS.”

Okay….Well, I see through the BS too but I do what I have to do to get by and that means corporate life right now. I don’t have the option of living in a “family owned” unit if I want to stay in Chicago. A corporate job is how I keep a roof over my head, heat coming through the vents and food on my table. It is also the reason I am able to travel, go to the theater, eat out at restaurants with my friends and support nonprofit organizations with missions I am passionate about.

These things matter to me. I don’t want to give them up or work harder to pay for him to do these things with me because he cannot afford them on his own. And not because he can’t find a steady job, but because he doesn’t want to. A lack of motivation and drive to continually improve is such a no-go for me. My sister tells me I am too picky when it comes to dating but I am looking for a relationship where either party is able to pick the other one up when needed. I do not want to have to do all of the picking up.

Is that too much to ask for?

The Result

I had a really good time on our date. We said our good-byes and parted ways after the game. Before I went to bed, I sent him a message letting him know I got home and thanking him for a fun night. I also told him the truth. I am uncomfortable dating him right now due to his employment situation but I would be interested in being friends if he wanted to meet out for drinks and sports watching.

He sent me a message this morning declining the offer. He doesn’t want to be just friends so that is that. I appreciated his honesty and I hope he appreciated mine as well. I feel like we left things in a good place and I can move on in peace.

Who knows, maybe we will go out again in another two years?! Dating after forty is full of unexpected turns apparently so it could happen. I promise to remember him next time though.

For now, onto the next one.

Speaking of my love of going to the theater (as mentioned above), I wrote a post listing my favorite and least favorite Broadway shows of all time. You can check out that post here! You can also check out a letter I wrote to my younger self here.

Dating After Forty Profile Picture
This is the profile picture I use for my Coffee Meets Bagel profile. And yes, that is a faux fireplace behind me. My team built it as part of our holiday decorations in December.
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Meet Carmen

I’m Carmen, the founder of this blog and the Vicariously Through You community. I am so glad you’re here!

I currently live in Chicago, IL, USA with my Maltipoo pup, Stella. I am 40-something, single and do not have any children.

When I am not working on this blog and growing the Vicariously Through You community, I work as a Financial Analyst. In my free time, I travel as often as I can, often as a solo traveler. I enjoy rainy days, plain green tea, Chicago Cubs baseball and books with happy endings.

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