Dating in Your 40’s – The Ugly, Part 2



Mr. Bitter Angry Dude


How to spot him:  You can tell them right off the bat though, because even on the first phone call they’ll nastily correct you about weird stuff or start an argument about the most innocuous of topics. A conversation with them might go something like,  You: “So, how do you like your job?” Him: “My job? Why would you ask about that? I thought we were trying to get to know each other personally. I don’t want to talk about my job!” Yeah, run.

Why he’s tempting:  It’s not – unless you are a lawyer.

Why you should steer clear:  I don’t know if it’s that guys this age have seen a lot of relationship disappointment that has made them bitter and angry, or if their bitter/angry vibe is what makes women run from them to the point where they are still single at 40.

Mr. Flake


How to spot him:  This is the 40-something man-child who still doesn’t know how to make plans in advance and can’t stick to any type of schedule. He’s the guy who says he will call you Monday night and then doesn’t. A week later, he emails you, “Hey, what are you up to?” You explain that he never called, so why is he asking? He apologizes and says he will call you that night. He doesn’t. A week later, he emails again, saying, “Hey, want to meet up?” You explain that you still haven’t spoken yet. He says — well, you can guess. It goes on like this into infinity.

Why he’s tempting:  Only he is damn good looking.

Why you should steer clear:  Infinity, it is worth mentioning again.

Mr. One Who is Still Married


How to spot him:  He will say that his divorce is about to be final and has been separated for a long time.  

Why he’s tempting:  Because you want to scoop up this prized possession before anyone else can get to him.

Why you should steer clear:  And if they say they’re “separated” or “in the process of getting divorced,” stay far away. Newbie divorcees are NEEDY.

Mr. Total Package


How to spot him: He has one hell of a career going and went to a top college. He is an athlete, a musician, and an avid traveler. He is handsome—and you better believe he’s well-groomed.

Why he’s tempting:  There’s just one thing he seems to be having a hard time finding—a girl worthy of his greatness.  Could that be you?

Why you should steer clear:  Yes, the woman fit for him will be the ultimate icing on his cake of perfection. He imagines her often—gorgeous as they come, she turns heads; bursting with charm and charisma, she lights up every room she enters; she’s a brilliant rising star in her career and beloved by her many friends. And that’s just her public persona—at home, she’s fantastic in bed, a spectacular cook, loving, selfless, and devoted. Oh and she also speaks French, plays tennis, sings beautifully, reads voraciously and she’s a history buff. His Juliet.

Unsurprisingly, he is single. He’s immersed in a fierce battle between his superhuman standards and his terror of being 40 and single—because 40 and single is not supposed to be part of his story.

Mr. One with the Psycho Ex


How to spot him:  No matter how nice he is, if your his ex-wife inserts herself into your relationship, you’ve got big trouble.

Why he’s tempting:  The key to navigating this scenario is to observe how your man acts when his ex’s unacceptable behavior occurs. If he takes a strong stand and takes steps to put a stop to the behavior, you may have hope.

Why you should steer clear:  The psycho ex may stalk you, harass you, or involve his kids in sabotaging your romance. Often, she’s still in love with this guy and perceives you as a threat, trying to steal him back though they’ve been divorced for years.  If he throws up his hands in surrender, and lets it all continue – face it, you’re doomed. There is no reason you should have to endure a meddling, intrusive ex-wife.

Mr. Player


How to spot him:  He’s the unusually friendly guy who makes effortless chit-chat, has expensive shoes and a good haircut—and is always ducking outside to talk on his cell.

Why he’s tempting: You know how in tennis when you play with a great player, you don’t suck as much as when you play with a beginner? Same applies here. If your date is a smooth operator who’s never at a loss for words, you’ll feel more relaxed, witty, and confident.

Why you should steer clear: Slick guys love dating. But they are less fond of relationships. If your pro dater has had a ton of 5-minute partnerships, doesn’t open up, or shies away from discussing personal details, he probably won’t commit.

Mr. Angry-I’m-Divorced-Too


How to spot him:  He’ll tell you within the first ten seconds that his wife ran off with her trainer. Or drained his bank account. Or both. And he can’t wait to hear all the ugly details of your divorce.

Why he’s tempting: You have a common enemy: The ex. And a heated trash-your-ex fest can get you all hot and bothered—in a good way.

Why you should steer clear:  If he’s still raging about how she did him wrong, he’s got, ahem, some issues to sort out. A lot of the divorced men I meet are eager to have dump on your ex sessions.  But I steer clear of anyone who is harboring that much hostility toward their ex, because they obviously aren’t ready for a new relationship.

Mr. Best-Friends-with-His-Ex


How to spot him: He’ll nonchalantly works her into conversations: “My ex thinks I should buzz my hair,” “When my ex and I were having lattes yesterday…”

Why he’s tempting: He sounds so enlightened! You think you’ve stumbled upon the most forgiving guy in America.

Why you should steer clear: Staying friendly after a breakup is a good thing, sure. But if his former wife still occupies the role of trusted advisor — Condoleezza to his George W. — beware. This is a guy who’s still in love, plotting a comeback, or at least hoping for the possibility of breakup sex.  Take a Pass on this one.

Mr. Crazy-Possessive


How to spot him: When he hears you were married, he jokes, “Did he hurt you? Just say the word, and I’ll get the guy.”

Why he’s tempting: Jealousy can be flattering as he wants you all to himself, which can be flattering and an ego booster.

Why you should steer clear: Intense jealousy is often a sign of emotional instability. Controlling people are usually very smooth at first but after they charm you into bonding to them, the control can turn very unpleasant, and even lead to stalking or abuse. So consider yourself warned!



About Hiding2014-2016

2016 Life is what it is and you just have to get through it. 2014 I started blogging just a short time ago, it actually feels good. I've made some new friends and soliciting feedback from others who have experienced similar life events helps me to not feel so alone. So we all have bumps in the road, we make poor decisions - we are only human. It is these life experiences who make us who we are today. There is no need to have regret, just move forward. Ok, easier said than done, because as you read my profile, sometimes I take a step forward and then two steps back.

Posted on January 12, 2017, in Bad Boys, Bits and pieces, Bullshit, Care, Chuck Taylors, Cool Chicks, Cool girls, Dating, Divorce, Divorce Sucks, Feel better, Furry, Fuzzy, Happy, Health Relationship, Healthy Relatinships, Love, Mate Selection, My Life Over 40, Nice Guys, Rebound, Relationships suck, Smart Women, Smarty Pants, Weekend, What women want, Whole again. Bookmark the permalink. Leave a comment.

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