Cleavage Selfies & Other Ahas

One guy’s lessons learned from online dating

Bill Jensen
True Story

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Two sets of full-disclosures up front:
• I’m well past the north side of 50. So, while I agree with Robin Williams— (God gave men a brain and a penis, and only enough blood to run one at a time)—I would hope that, by now, my well-traveled (well-worn?) soul is searching for things more robust and meaningful than just satisfying carnal needs.
• I really don’t like this search thing. Divorced after 27 years of marriage and then another six-year relationship: I’ve figured out that, while I first need to be happy and fulfilled as an individual, I really am designed to be part of a long-term relationship. I’m a better me when in that state. And while I always enjoy meeting new people, actively searching for that partner can sometimes feel more like work than play!

Still, I forge on. Sometimes in social settings. Regularly, online at places like Match and OurTime. Here are a few of the things I’ve learned…

Cleavage Selfies: Women’s Hidden-In-Plain-Sight Marketing Secret
At least 80% of all the profiles I see, or who check me out, have at least one cleavage selfie. (And these are not college girls. These are women between mid-40s to 60+. Lawyers. Bankers. Dentists. Accountants. Entrepreneurs. Chefs. Schoolteachers.)

Is somebody teaching a class on how to take these pix? Because they all seem to be the same photo: Woman, arm extended about a foot and a half above her head. She’s smiling wonderfully at the camera. (Lovingly at me, by proxy.) At first it appears she wants me to focus on that beautiful smile, that happy face. But wait. There’s the real focus. I’m looking down her shirt. Often, with at least one or two unbuttoned buttons more than in the other shots. Pushed up and central to the photo. Cleavage. Very consciously positioned by the photographer.

And you know why it’s there? Like all good marketing efforts: It’s there because it works! I DO linger on those cleavage profiles longer than the others! (Robin Williams: I bow to your wisdom.)

We’re All Animals
I’m big into feelings. Mine and hers. And, since I’m seeking trust and caring and sharing and happiness beyond casual dating, I try my best to create those things for her too. So I approach meeting each new person that way.

But what I’ve discovered is that while ALL women care deeply about how deeply you care about her — by mid-life, they’re also in touch with their animal instincts. I’ve been completely surprised by how quickly and easily she will talk about sex. By how quickly and easily phone sex happens. By how quickly and easily casual sex happens.

What I’ve discovered is that, by mid-life, most women have a very healthy relationship with their animal side. That if there’s an attraction (chemistry is EXTREMELY crucial) and trust, her sexuality and her needs are front and center.

Be Vulnerable, Earn Trust
I begin each new conversation speaking to that person about things that are way beyond “what’s your favorite music?” or by sharing things that I wouldn’t want shared in a public forum. This isn’t for everyone. (For those who aren’t good matches for me, I’m told I shared too much, too fast.) But for most people who’ve lived a full life before I meet them, I’ve found that being extremely open and vulnerable, and trusting that person with your inner self, that that trust and openness is returned.

We All Have Baggage. What REALLY Matters?
I have baggage and am a flawed human being. So does she, so is she. What I’ve learned is that for each of us, our job is to know — deeply— the one or two or three things that matter most to us, and explore those things up front with the other person. If there seems like a match, cool! Keep going. If not, that’s also cool. Maybe you’ve found a new friend.

But beyond those precious few things, most of the things that might have bugged us about a partner in our 20s or 30s or 40s, really don’t matter. Life is too precious to keep carrying crap around in bags and keep focusing on it.

Focus on what really matters. Let go of everything else.

Dad Talk is Turn-On Talk
I have found that the more I share about how I’ve enjoyed being a dad; what I’ve fucked up as a dad; what I think I did well as a dad, etc. — the more she opens up, on all levels. (Keep in mind, most of my potential partners are moms whose kids are young adults.) I’ve learned that women can quickly figure out what kind of person you are, and what kind of potential partner you’d be, by knowing alot about what kind of dad you are.

Family Matters, Only Differently Than I Imagined
Whenever I do find someone, I hope it’s for the rest of my life. I really hope the next love of my life will be my last love, the one who will cradle me as I die. That she will be my closest family.

I always knew that family was crucial to me. But, until recently, I never realized how fluid that would be. One kid turns to me as Dad a lot more than she does with her own Dad. I’m as close to my ex-sister-in-law as I am to my own sisters. Not worrying about or for my son is still hard, even though he’s 27, and is fully in charge of his life. My new partner will likely have kids, and hopefully I’ll be forming a wonderful relationship with them.

Even though, as a professional, I coach executives and organizations on change — I still struggle with a major change myself. That the depth and intensity and amazingness and pure joy of family love has happened very differently than I imagined it would. Not better or worse. Just very different.

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Bill Jensen
True Story

Makes it easier to do great work. Hacks stupid work. Author. Speaker. Loves life, family, fun — everything that matters.