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The blurred lines of romance as a single, divorced mother reinventing herself

Updated on August 7, 2015
Woman contemplating about life.
Woman contemplating about life. | Source

So you're ready to go back into the water. Even with sharks?

Just when you thought it was safe to enter the dating pool again...

It's been over five years since my ex left on a bright Christmas day. The memory was forever etched into our minds (my three kids and mine). After I had snapped out of the incessant self-pitying and non-stop crying, I was ready to dip my toes into the dating pool again.

Or so I thought.

My first love post separation was the most rewarding, self-discovering and romantic thing that happened to me even throughout my marriage. I was grateful for the nuggets of wisdom I learned right away from a caring, considerate and lovable guy I still call my "dark knight." I know he still keeps tabs on me, checking in every now and then to see if I'm happy. Let's just say he chose the path right for him and I ended up as the one who will always wonder "what if" we could still be together.

Then came the freak show of dating nightmares like the never-ending clowns from the mini car at the circus.

The following years proved to be both disastrous, and sometimes sweet and enlightening in my many attempts with online dating, or organic dating with men I met in person (let's just say the men you meet in a bar usually aren't Prince Charming). Here's a compilation of men I've experienced, why they weren't a good match, and what I learned from them:

  • The body-builder. He was 6'4" and built like a duplex. He posted pictures of two women on his two shoulders (while we were seeing each other). Although he was sweet and very helpful to me (like when the flood entered my living room by shoveling water away from the house) I was turned off by the fact that he showed up tipsy in the middle of the night. He actually broke things off with me in a text message, saying we should "take a brake" (yes, that's how he spelled it), but then called about a year later trying to reconnect. I even agreed to another chance but when he said I would have to drive us on our date because he just got a DUI, I kindly refused the invitation. What I learned: Men are chivalrous by nature and he was a giver. One of our first dates was a side-by-side massage that helped me relax because he knew he was dating a stressed, single mother. I learned to appreciate (and accept) when a man wants to be generous and take care of me. I also learned that addictions are deal-breakers for me.
  • The ex-con son of the religious couple. The chemistry was unavoidable and being a fellow Taurus, I melted under his presence and passion. The deal-breaker came when he took off with a loot of my cash kept at home. I was grateful to get it back by his religious parents, but the lesson I learned was scary and high stakes. What I learned: Take it slow with a man you're truly attracted to. The blue eyes, tall, slender build can create instant chemistry, but don't succumb to someone you know nothing about, especially if he invited himself into your home (and your kids don't like him).
  • The sweet, innocent military guy at the bar. My first one night stand was quite a new experience, but one I'll never regret. He batted eyes with me at the bar on the beach days after I'd been catfished by a married man who led me on in emails and phone calls for several months. Needless to say, broken hearts can be instantly repaired by meaningless sex with a cute guy who thinks you're much younger than your years. What I learned: It feels REALLY GOOD to be appreciated for how well you keep yourself and be told you're beautiful. Telling a guy you're 39 and him saying, "you were the prettiest girl at the bar" is worthy of a sweet tale of romance. Even if it lasts a night.
  • The 27-year-old male model. First of all, I want to say that every midlife woman who becomes single should know what it feels like to make love to a hot, tight body. Period. The ability to be aroused just by seeing an attractive man who wants to make love to you is one of the things every woman should have on her bucket list (if you married a man and never had this experience, wow, you're missing a great orgasm!). What I learned: Men who are good looking may turn you on instantly but it doesn't mean they're the best lovers. In fact, most are so used to getting anyone they choose that they don't develop exquisite lovemaking skills. Chock it up as a good eye-candy fest but don't expect miracles from good looking men. He did the Houdini Act and disappeared. Enough said.
  • The hot, young thing with the tongue ring. I was a bit curious and perhaps anxious from doing online dating for a couple years when I gave him a chance meeting. Needless to say, I didn't regret it. He may have been young in years, but he was definitely skilled beyond them. What he knew more than the peers in his age group: Pleasing a woman is more important than your own pleasure. I appreciated that he put my needs first, and in return, I showed my gratitude. That's what good lovers do: It's a give and take, reciprocated. What I learned: I wish I was about 20 years younger. I don't want to be seen as the older woman, so our meetings remained covert, but sweet and intense.
  • The village idiot, AKA regular drunk at the bar. I'll call him Victor. We met a couple times at the bar when a coworker was playing with his band on weekends. He bought me an appletini multiple times, but I saw him inebriated and flirting with everything female that rolled through the dive, so naturally my eyes rolled the other way. After a few weeks of fun, I noticed a funny thing about his priorities: He would be toking in the living room while I lay naked in his bed. So I knew we weren't a good match. Although he did the fade-away on me, he saved himself a bitter burn by a woman who is not into drugs or disrespecting your significant other. What I learned: Some men use money and power to appear attractive (especially when looks no longer serve a purpose). Don't be fooled by a man who spends $100 for dinner and drinks but treats you like you're invisible.

Not all experiences need to be painful as I learned there are many of us going through similar emotions.

The college crush. He was everything I could have wished for in a man (at 20). Witty, worldly, long locks of hair draping his deep, intense stare. He flirted with every girl in the journalism class. But I fell for him, then, and 23 years later when we reconnected on social media. Love isn't perfect but it's wonderful to have perfect days with someone who cherishes you, especially after you've both been burned by love in the past. What I learned: Older men tend to know what they're doing in the bedroom. If they've been a giver with other women who used them in the past, they're more likely to appreciate your sweet nature and pay it back tenfold. As will you that your needs are being met.

So what have I learned in these experiences?

I've mostly learned about myself: what I want and what I don't want. The same goes for any woman (or man) going through divorce, has kids and wants to have a happy experience at some point along their swim in the dating pool again.

You can learn to recognize the traits that turned you off in your failed relationships from early on as well as be mildly surprised by loving gestures felt for the first time by those who genuinely care about you. These are the steps you take to go upward to a higher awareness and find the kind of relationship you truly desire in the second half of life.

Be prepared for drama, chaos, some joy, but also a lot of disappointment before you meet the one just right for you. He is out there. Or she. Don't ignore red flags. Your gut will be screaming them to you often enough; you just need to listen.

On a final note: love is a mystery. The answer is held in each moment you spend.

Love the second time around

Love is waiting to happen. Don't let bad experiences keep you from finding the real thing.
Love is waiting to happen. Don't let bad experiences keep you from finding the real thing. | Source

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Love again

Cheers to love again!
Cheers to love again! | Source
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