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

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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 #4:

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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Things to Do for a Date Night That Don’t Require Money

I may receive compensation from links on this site. See my disclosure policy.

As Valentine’s Day has long been prized as a consumer holiday in the United States, it can put pressure on couples to spend money – even if it’s money they don’t have. But Valentine’s Day doesn’t have to be about expensive dinners, flowers and chocolates.
Things to do for a date night that don't require money - Realistic romantic ideas that couples can do together without spending a penny
Photo Credit: Rebecca D. Dillon, author of Soap Deli News Blog

It seems like so many things have changed now that technology has replaced books and libraries, land line phone conservations, and play time has become indoor video game time – even television has replaced family time. Additionally, as a society, many of us have become so focused on consumerism we have lost sight of the important things – those little things we had and did together before technology made everything immediate and easy. Lots of people don’t seem to appreciate the simple everyday, mundane things the way our parents and grandparents did. We have forgotten how to appreciate life for the gift it is and don’t feel fulfilled unless we own more than we can actually afford. This lifestyle of easy credit, technological advances and living beyond our means has become the norm. And now that we are in a recession people are feeling their pockets pinched or have lost their jobs and are struggling to continue living beyond their means.

Knowing so many people are still out of work despite continuing look, the families that are working or on a fixed income but still struggling, and even those of us who have all we need and even the things we want, but want to remember what’s really important in life and get back to basics – to the way things were before the noise of telephones, computers, video games, and television. I wanted to find ideas for couple date nights that really truly didn’t require any money at all and at the same time didn’t leave anyone feeling slighted because they don’t own a tv, a computer, or even a car.

So I posed the following question to friends and family through my social networks.

“What date night ideas do you have for couples who have only the basics and no room for a budget budge? I want to hear your date night ideas for a couple that does not own a working television or computer, cannot do outdoor activities due to bad winter weather, cannot drive anywhere as either gas is too expensive or they don’t own a car, do not own board games and have no money to buy them – not even a deck of cards. Money is also out for grocery trips and alcohol. What are your ideas?”

Some of the responses I got were as follows:
DIY Ideas for a Romantic Date Night That Don't Cost a Dime
Photo credit: Lime Lane Photography
  • Read a book to one another – either one on hand or borrowed from the library.
  • Assuming you own a deck of cards, play strip poker. 
  • Listen to music – like the “golden oldies” of your childhood and dancing.
  • A dinner of beans and rice, Hollywood music, dancing under the moonlight and a candlelit massage.
  • From my sixteen year old son – writing or drawing your feelings for one another or – and this shows you how awesomely geeky my son is – write a computer program that does the same.
  • Sex. (You had to know that one was coming.)
  • Asking one another more intimate questions about their lives.
  • Make your own board games or a deck of cards with paper, pen and everyday objects. Play charades or Pictionary with pen and paper. The person who loses makes the winner and him or herself dessert.
  • Painting. (No paints? Is there something in the house – like paprika – that can be added to water to create a pigment?
  • Plan a dream vacation together – even if it’s not an option in the near future.
  • Camp out in the living room with a tent – either real or one made from furniture and sheets. Light candles, make smore’s or whatever is on hand, and tell ghost stories.
  • If musically gifted, craft a song together.
  • Have an indoor picnic with sandwiches and cocoa and discuss creative ideas.
  • Invite over other couples and have a mystery murder night where you organize a cluesque play. These are fun and you can do them in any time period for little or no more as they are more about imagination and intrigue with your closest friends. A reader would hold hers in the Victorian period.
  • Work on a diy project together.
  • Give a spaghetti dinner an Italian theme and play Sinatra or Dean Martin and cook a spaghetti dinner together. Decorate the kitchen or dining room like an Italian Bistro.
  • Think bath tubs and massages and let your imagination run wild.
  • Take a bunch of old photos out of storage – whether digital or hard copy – and make a memory scrapbook of your time together. Remembering better times and even leaner times can help acknowledge strong bonds and overcoming challenges together.
And of course I have been brainstorming for ideas of my own. When I was trying to come up with ideas I went back to the things I did as a child for ideas. I could take nothing and turn it into a happy world of fantasy and play.
I remember digging up dirt and mud in the yard and mixing it together with grass to make pinch pots that I dried in the sun. Then I’d serve dinner with large leaf weeds as salad and the seed tops of plants as beans. I also made grass dolls.
I would draw out foods on paper along with dishes and silverware. Then I’d create menus that I gave to my family and would serve them dinner in the hallway on the floor where I’d created my restaurant. 
I took newspaper and masking tape and aluminum foil and made a mermaid’s fin to fit myself – it was the 80s and Splash was huge! – and then wore my bikini with my mermaid’s tail to start off a magic show that I invited all the neighborhood parents to. I introduced the show by jumping out the tail and becoming a “human” and then me and all of my friends performed magic tricks right on the back deck of my house. 
I even created my own science museum once by gathering interesting objects I found in the woods behind my house – including an opossum skull! I displayed everything in my tree house neatly lined up on a table with cards that stated what each object was. 
I loved playing with Hot Wheels cars too, so I would tape pages and pages of paper together and draw roads and houses and parking lots for them to drive on. 
I made my own paper dolls for myself and my friend, Jenny, that we could cut out and play with. there were even scenes to cut out and set up. We each had a character – one was Autumn and one was Benita – and I think (it was a long time ago) my character was named Autumn and hers was Benita. 
For a class project in elementary school Jenny and I created a slide show together of a story we wrote and illustrated. We photographed the illustrated pages of the story and had them made into slides – film strips were so big back then! – and then recorded the story onto cassette tape. I made the “beep” that indicated when the next slide was to be shown using my Magical Musical Thing. (Does anyone else remember those?) 
During good weather I’d take chalk and draw roads all over the cul-de-sac for my friends and I to “drive” on with our bikes. I even drew parking lots and houses that you saw from a bird’s eye view so every room in the house looked like you could interact with it. I had so much fun drawing couches and toilets that you could sit right down on!
Wouldn’t it be wonderful if we could regain that childlike enthusiasm in our everyday life? I thought it would be so I pulled some of my own ideas from my past experiences and thought of ways to apply them to the here and now. But I also pulled from things I’ve experienced as an adult that always make me smile. 
  • Dance like no one is watching. It’s a popular saying, but if you really consider it and can actually do it, it feels so amazing. I used to dance in my bedroom with the music blaring but I never danced in front of anyone at all. I was that girl that stood shyly by the reception table or sat on the bleachers during a school dance. I was a wallflower – though I imagine that the people who know me now that didn’t know me back then might find that hard to believe. I did not dance publicly in front of anyone until I was in my 30s. And once I started, I didn’t want to stop. I literally started dancing for me and danced like no one was watching. And now I have the best time dancing when I do. So just dance. If you and you’re partner can’t dance – do it anyway. Learn together. There’s no better way or better time to dance then in the here and now with someone you love. Do it dressed up like you are going out, but then stay in.
  • If funds don’t allow springing for a special date night dinner, make a regular dinner special. Eat by candlelight. Design your own special place mats – together – for the event even if it’s on paper. Serve paper lobster tails with your beans and rice. Dress up your dishes for the occasion by drawing your favorite memory with your partner onto your mugs or dinner glasses with a Sharpie. Drink water out of wine glasses. But for every step you take to create dinner, do it together. Want a surprise for one another? Create your surprises in separate rooms at the same time. Then play twenty questions to see if you can guess your partner’s surprise before the reveal!
  • Bring summer to you by covering the windows with paper and then drawing a spring or summer scene – whatever your favorite season – on the paper together and color it in. Then camp out indoors or pretend you’re at the beach.
  • Do what you usually do but explore ways of doing it without any electricity or modern conveniences. How many creative ideas for day to day living can you come up with and execute together? Dig out that book of survival skills you have in case of a zombie apocalypse and learn how to become more self sufficient together. 
  • Create crossword puzzles or word searches for one another with words and clues that are relevant to your relationship together. 
  • Write a radio “play” together that includes homemade sound effects. (I remember doing this when Star Wars came out. One of the children’s magazines I read had a script to go bar and instructions on how to make the sounds so they sounded realistic.)
  • Turn books and other everyday objects into building blocks and see who can build something that stands the tallest.
  • Give one another tattoos with non-toxic markers. (I actually did something similar to this once and took my colored Bic markers to a local bar on karaoke and let people color in my tattoos. Everyone ended up drawing their own tattoo creations onto everyone else.)
  • Work on DIY project together. See what kinds of materials you have around and research fun things to make with those materials. Or raid the pantry and cook up something you’ve never made before like marshmallows or caramels or creative jello desserts.
DIY Zentangles Valentines Projects - Create Zentangle Hearts with Your Significant Other and Decorate Your Home for Valentine's Day
Photo Credit: Punk Projects Blog
  • If weather permits, use chalk to draw a game board – chess, checkers, etc. – on a sidewalk or stoop and use rocks and other items as game pieces. 
  • Use pages from old magazines to piece together your dream home room by room.
  • Make weapons from office supplies and have a pretend war. (There is actually a free ebook available right now on this very subject called Office Weapons.) 
  • Create a paper fish aquarium and fill it with hand drawn paper fish and coral. Each of you can make a kissing fish then pair them together! 
How to Make Banana Oxidation Art - Source: Instructionables.com
Photo Credit: Instructables
  • Draw images of one another as a couple onto bananas then photograph and frame. You can easily draw on a fresh banana with a toothpick and your image will “magically” appear later. There’s also a video tutorial on how to do this at Instructables. Don’t have bananas? Draw caricatures of one another.
  • Create a comic strip or comic book together about some of your amazing adventures – real and imagined – that you’ve had together. This is a creative way to document your favorite memories without photography or the expense of a scrapbook and supplies.
  • Create a “museum” of your memories together by finding objects that are sentimental to you, arranging them on a bookshelf and attaching little notes to them in regards to the event or why they are special.


The possibilities of things to do while staying in are endless. You just have to have a little imagination, an appreciation for the little things, and be fearless in the face of silliness!

If you’re looking for ways to save money either to necessity or by desire to simplify your life, I highly recommend the book, How to Save Money at Home: A Room-by-Room Guide to Cut Spending, by Kim Parsell. It’s currently available as a free ebook download from Amazon. (You can download the free kindle reading app if you don’t own a kindle. I use the app on my macbook.) You can also find a few ideas in my blog article, Frugal Ideas for Saving Money

If you’re looking for homemade Valentine’s Day gifts to make and have the extra room in your budget, I hope you’ll check out my diy ideas for homemade Valentine’s Day gifts. And remember that by buying and shopping locally and from small business owners, you are helping families and communities right here at home to live better lives.

Do you have other creative ideas for a winter weather date night that doesn’t cost a penny? Then please share your thoughts in the comments for the benefit of others looking for things that they can do together!