I Dated A Guy In His 40s & He Was Just As Immature As Some Guys In Their 20s

I’d had enough of immature guys and thought that dating an older man would solve most of my dating problems. Turns out, age really is nothing but a number—this dude was just as bad as all the younger ones I’d been with.

  1. He asked my friend for my number instead of asking me for it. We met out at a bar one night and we had mutual friends. It was our first time meeting, but he seemed into me and I thought he was pretty cool too. A day later, my BFF told me that he asked her for my number. How very high school of him. I gave her the go-ahead; I was curious about dating an older man and I figured I’d give it a go. I wasn’t on the hunt for a boyfriend, I was just looking to have some fun and this seemed as good of an opportunity as any.
  2. My BFF warned me he was a player. He was 42 and had never been married. I didn’t judge him for that but I took the fair warning from my best friend. He seemed to be the toxic, non-committal bachelor type of guy that I was used to. Still, I wasn’t planning on getting serious with him so it was no big deal. I thought maybe he could teach me a few things I didn’t already know. I was eager to go out with a mature guy who was more experienced in life and love than I was.
  3. He invited me out on a non-specific “date.” Instead of asking to meet him for dinner or drinks, he just said, “We should go out.” He never gave a time or a place, just mentioned something vague about a Thursday night. It was the typical ambiguous invitation of players everywhere. That night, I waited for him to text… and waited some more. I assumed I’d hear from him by early evening but I didn’t. I finally gave in and texted him. I was annoyed, so instead of waiting for him, I decided that I would just text him and tell him to GTFO. He texted me back immediately, apologizing and explaining that he was out at dinner with a friend. Uh, WTF? He begged me to let him make it up to me and admittedly, we did have a great time.
  4. He was just as arrogant as men half his age. I couldn’t help but think he was testing me with how he acted on the night of our first date. He seemed to get off on a younger woman being into him, but I told him that either he was going to act like a gentleman or else I wouldn’t be seeing him. I was definitely attracted to him and I had a lot of fun with him, but my expectations of an older man were higher. I made sure he knew that I could easily find another guy, so if he wanted to see me, he’d better step up his game. Thankfully, he did.
  5. He made things sizzle for a few weeks and then pulled the slow fadeWe saw each other for a few weeks. He texted me every day, bought me gifts, and took me out to nice dinners. I was into him and it seemed like we had a nice little thing going, but I always made sure not to start developing any real feelings. Admittedly, I’d gotten used to all of the attention he lavished on me and I’d come to expect his texts. After a few weeks, I noticed a dropoff in the amount of communication we had. Our dates were fewer too. I didn’t really think too much of it, but it eventually became clear that he was purposely pulling away.
  6. He eventually stopped talking to me altogether. It was my best friend’s birthday and we had plans to go out. He was invited and I’d hoped he would come with me. After not hearing from him all day, I finally texted him to remind him of our plans. He claimed he couldn’t come and blamed it on a minor car accident he’d had. He had another car, so it wasn’t like he couldn’t make it, nor was he hurt. He decided to stay in and sulk over his dented car but also insisted on receiving sympathy from me. I didn’t give it to him. I went out that night and I just had a feeling that we would never speak again. We never did.
  7. He never gave me an explanation. He simply stopped all communication with me and never told me why. I was left wondering and I was pretty annoyed, although I had to remember that I’d been warned. I actually developed feelings for him and wished we could keep our little fling going. I never wanted anything serious but I enjoyed our time together. I suppose I had certain expectations of him since he was older. I figured he would be more mature in terms of dating and transparency but he wasn’t.
  8. I later found out he was still seeing his ex. We weren’t exclusive so I wasn’t hurt by this, but I felt like I was used as a stand-in, a distraction for him, and a tool used to make her jealous. He was not only still seeing her, he was fully obsessed with her. He was having a relationship with her while she was still married and was seeing me on the side. It dawned on me that he was emotionally needy. He didn’t want to commit to me yet he wanted my attention. He tried to hook me in by playing games from the beginning. He wanted me to chase him, to lavish him with attention, and he seemed to need the ego boost. What an a-hole. Turns out, older guys aren’t more mature after all.
Fierce Writer | Coffee Snob | Digital Nomad | Solo Traveler | Self-Improvement Junkie | Lover of Books | Beginner Yoga is my jam