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Online dating in your 40s is the equivalent of running head first into a brick wall. It leaves you dizzy and confused, wondering just what the F happened. Everyone has baggage. Some people though, they have something inherently wrong with them.

Online Dating in Your 40’s Is The Equivalent of Running Head First Into a Brick Wall

My boyfriend and I both tried online dating. This was prior to meeting one another through, well, online dating. Apparently he stuck around because he thought it was refreshing that I wasn’t fake. There was no pretense. Just me in my, sometimes overwhelming and slightly obnoxious, glory. Greg and I have been dating for around five months or so. I can’t give you an exact time frame. Something that Greg is always (teasingly) giving me flak for.

Online dating in your 40s is the equivalent of running head first into a brick wall. It leaves you dizzy and confused, wondering just what the F happened. Everyone has baggage. Some people though, they have something inherently wrong with them.

The other day I asked Greg what he liked about me. You know’ what really made me special to him. I often give Greg flak for being absent from social media. Plus, poor guy, Greg has like one friend here, having moved from Atlanta. So I wanted to be sure he wasn’t hanging around because he was lonely or some silly nonsense.

As Greg has only been living in Virginia since December, it’s completely plausible that he’s with me through my indecisiveness and hormones for purely selfish reasons. Although, he did let me slather him in sunless tanner, take photos and then write a tell all.

Tell me why you love me.

“So. Why is it EXACTLY that you’re with me?” I asked the other day.

His first response? “Well,” he said, “you have a dog.”

Okay. I get that. My dog is pretty awesome. (He’s a dachshund after all.) So I guess I can let that slide. I mean, quite honestly, I would NEVER date a guy who owned a cat. Not that I hate cats. I just think dudes that have cats are a little off. Allergies aside, there’s just something weird about them that doesn’t mesh well with my personality. So when I was swiping left during this whole online dating debacle, then left again, then left again… (Le sigh.) Anyone who owned cats was an automatic no. Of course, mostly everyone else was too.

“So what else? You can’t JUST be with me for my dog.”

(My dog on the other hand thinks he’s people, so he’s finding the whole first answer thing totally plausible. However, here I am thinking that his next answer better be something about me specifically or I’m walking right out that door.)

“I really like that you’re outgoing. It helps me out because I’m shy and don’t know what to talk about in a lot of situations.”

Whoa. Hold up. Let’s stop right there before you dig this hole any deeper. These answers weren’t exactly what I was going for. For someone who doesn’t forget birthdays or holidays, is generally romantic and occasionally passionate, I was expecting a much different answer. But hey. He likes Star Wars and he can cook. Which, according to my friends, are apparently two very desirable traits to have in a boyfriend. (Or anyone for that matter.)

So, just how did I get here? Well, that requires a little back story.

Into the (not so) way back.

My BFF Bambi (who is not a stripper but an educational director at the zoo – and yes, that is her real name) had been on OK Cupid after she and her second husband split. He was a nightmare, unfortunately. Both a drug addict and emotionally abusive, this guy actually treated Bambi worse after she developed breast cancer. Luckily the judge had enough sense to see this and ordered him removed from the home.

Prior to that, however, she had been staying with a friend for her own safety. All while she continued to pay the mortgage and all of the utilities on her house while her ex-husband lived in her home, rent free. Within that time frame that she stayed elsewhere, he not only stole from her, he also quit his job. He trashed her house and even went so far as to hook up with a fellow addict. A girl with an active felony arrest warrant for both for heroin and gun charges.

When Bambi’s ex, who quickly exhausted his own friend’s patience, finally moved back to Wisconsin to stay with his parents, it was one of her best days ever. Unfortunately, as luck would have it, her rebound was a two-faced liar and a possessive control freak. Which proves just how easy it is for any of us to fall back into that trap of emotional abuse. (Much like I did, myself.)

However, like me, Bambi is a fighter. She’s a scorpio and I’m a gemini. Together we’re tough as nails. But most of all, we are survivors.

Online dating in your 40’s is its own special version of hell.

As Bambi had been married for the past ten years, she was not in the know when it came to “modern day” online dating. So she asked me for suggestions. I gave her a few of my usual go to online dating sites and she signed up.

Then my own marriage, of just six short months, fell apart.

Bambi had been on a few dates prior to me moving in with her over Christmas weekend. My husband of six months and I split just a few week prior to that. I started therapy around the same time. So, as is the way of women, Bambi and I, both freshly single, found ourselves sharing too much wine one evening while simultaneously talking and laughing, discussing her dates and other general gossip that two best friends share.

This inevitably led to a discussion of online dating sites. Which were the best, which were the worst, and which ones had at least 3-5 people we knew. Bambi was particularly a fan of OK Cupid because of their detailed and EXHAUSTING list of personality and lifestyle questions. So, while in the midst being half drunk (okay we where schmammered) on wine, I signed up and we started answering question after question on my profile, together, laughing all the while.

While Bambi eventually met her now current boyfriend, it took me a while to catch up with her. Likewise, her online dating experience was not like my online dating experience. Because mine was a complete and total nightmare.

Let me tell you a little something about dating in your 40’s. Online dating in your 40s is the equivalent of deliberating running head first into a brick wall. It leaves you dizzy and confused, wondering just what the F happened. Everyone has baggage. However some people out there, well, they have something inherently wrong with them.

Don’t get me wrong. I am, or was, just as F’d up as the next person. I have my own baggage from some pretty messed up relationships that left me with me with my own set of PTSD symptoms. I mean my first husband contributed to me developing agoraphobia. He used to sneak into the bathroom while I was showering and scare the crap out of me – over and over – and even if I locked the door. So going into this whole online dating thing was like pulling out a bag of tricks and seeing which “me” was going to come out as a result.

Anxiety is a bitch. Online dating with anxiety is a bigger bitch. So I drank too much on first dates. And third dates. Basically, I relived the same cycle of madness from previous failed relationships until I found a holistic therapist that actually helped me. It wasn’t until Greg that I really started to pull my shit together. Everything before Greg, however, was a total mess. So I documented the hell out of my most interesting online dates in what I call “The Dating Files.”

Online dating in your 40s is the equivalent of running head first into a brick wall. It leaves you dizzy and confused, wondering just what the F happened. True stories of terrible online dates. #dating #onlinedating #disasters

The (online) dating files.

While Bambi and I were both able to navigate our way into healthy, happy relationships, there is some unfortunate drama that preceded those accomplishments. Here are a few of the worst.

Entry #1:

Sometimes swiping left works. Other times weirdos message you and you have no control over it. There was one guy with one of the worst dating profiles I’d ever seen. He told me that I would be perfect if I only smoked. He was non-mobile and a drug user, so, for me at least, I think the whole “non-smoker” thing worked in my favor.

Entry #2:

Another guy that I messaged a few times seemed normal, Not to mention successful. Just before we met for the first time however, he asked if I had a problem dating married men. I blocked him immediately afterwards.

Entry #3:

The first guy I went on an actual date with, after joining an online dating site, was an alcoholic musician. He claimed to have Lyme disease. Although he did lack the deteriorating health symptoms of undiagnosed Lyme. My guess is he actually has fibro. Buy hey, who am I? That being said, I understood the self-medicating thing to deal with pain. Unfortunately, I really think this guy just had a death wish. Not only did he love to drink and drive – because when did he not drink? He also never buckled up.

He wrote me the most beautiful song for Christmas about a week after we met. Regrettably this guy was not only a musician, he was also a narcissist. As if the alcoholism wasn’t bad enough (he’d crush beers in the morning to avoid DT’s) he made me cry three times over a four week period. The kicker with this guy was, on his online dating profile, he described himself as the perfect Southern gentleman.

There was also the story (and he LOVED telling stories about himself to anyone who would listen) about him drinking beer on his drives from Virginia to Tennessee. He’d occasionally take his elementary school aged daughter on these trips. To save time, and avoid stopping for pee breaks, he’d also have his daughter hold a soda bottle for him so he could pee while was driving. Yeah. No words.

The only good thing that came out of the few weeks I hung out with this dude was that Bambi was able to get her water heater, dishwasher and garbage disposal fixed. (Side note: Musicians, no matter how F’d up, are harder to ditch. My second husband included.)

Entry #4:

This next guy was an even bigger doozy than the last one. It started out with him telling me that I should talk to him on the phone because, back in my day, there no texting. Somehow, and it was probably the dry sense of humor, we did date ever so briefly. He was an even worse alcoholic than the first guy, with an unhealthy co-dependency on his younger brother.

We’d meet up for brunch on the weekend. What this actually meant was he was going to be wasted by 11:30am and he’d forget about eating entirely. He also forgot to shower. Or just didn’t care. He kept airline flight bottles of vodka in his car to drink on breaks. He was also waiting on a court date for his second DUI. And he’d scream at me just to turn around and beg me not to leave. If he thought I was mad the phone calls and texts were incessant.

I finally had to block him in the end. Sadly this was after having to give him a shower because he wasn’t physically capable and then help him locate his car the next morning.

Entry #5:

And then other guys still were simply just annoying because they were so indecisive. You can have a great white collar job, kick ass hobbies and be attractive, but if it takes a week and a half for you to plan a dinner date, I have to take a pass.

Final thoughts (and online dating advice.)

Someone once told me (see entry #4) that his Dad gave him this advice. “The quickest way to get over someone is to get back under someone else.” This is terrible advice. It’s also likely one of the reasons online dating can be so disastrous. This guy’s dad was not only emotionally and physically abusive, he also cheated on his wife on a regular basis. So you can see how unhealthy relationships lead to more unhealthy relationships in a cycle that never ends.

If you’re dipping your toes into the online dating pool and it feels like a trip through wonderland – raise your standards. Change your behaviors. Also, from personal experience, if you’re really angry about your last relationship, you won’t find happiness until you’re able to let that anger go. It’s a hard lesson. As is learning to change the thoughts and patterns of behavior that landed you in that mess to begin with.

Quite honestly, I met Greg because I started choosing guys who “weren’t my type.” And I almost missed out. Because, for me, it didn’t start out with that instant connection – that spark – that I was used to. Instead it was slow and steady. There was no rush to live life to the fullest like you’re speeding on coke because you could die at any moment. I had to step back, relearn and then move forward.

Finally, my therapist recommended the book, Stop Caretaking the Borderline or Narcissist: How to End the Drama and Get On with Life. If you find you’re also part of an unhealthy cycle, this book will help you see the other side of that so you can finally break free.

If you enjoyed this article, you may also be interested in my article titled, You Are Not a Failure.

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  • Jennifer

    August 3, 2018 at 12:35 pm

    When I started online dating in my 40’s, I had very specific no’s that I wouldn’t compromise on. Basically, anything my ex-husband did that I absolutely loathed about him, that was a NO. I didn’t want to end up with a repeat.

    1. Rebecca D. Dillon

      August 3, 2018 at 1:03 pm

      That is WONDERFUL advice! Thanks so much for sharing!

  • Susan

    August 3, 2018 at 7:51 pm

    I’ve always checked out your diy’s but this is the first personal blog post I have read from you. I love you even more now! What an honest and up front post. I glad your in a good relationship now and hope it works out for you. I was down a similar road after divorce number two also. On line dating is really scary especially for me as a repeat “offender” in choosing men. I ditched the whole idea and just let things happen. It took awhile as I am basically an introvert but I finally found someone. I will tell you that we have been living together for about 6 years and I have no desire to be married again. Thank god he is understanding of that. Good luck on your journey and hold your head high!

    1. Rebecca D. Dillon

      August 4, 2018 at 5:16 pm

      Thank you so much for sharing your thoughts. I’m so glad that your journey is also now a happy one and I’m thrilled to have you as a reader. 🙂

  • Susan

    August 3, 2018 at 8:02 pm

    Oh forgot to mention….the book that helped me and recommended by my therapist was Controlling People: How to Recognize, Understand, and Deal with People Who Try to Control You by Patricia Evans. I also read another of her books titled, The Verbally Abusive Relationship. Both were excellent

    1. Rebecca D. Dillon

      August 4, 2018 at 5:15 pm

      Thanks for the recommendations. I’ll definitely check them out!

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