It was 1982 and my college pal’s recently divorced Dad, a successful executive, was about to go out on his first date. “Dammit! Is this tie dimple precisely centered?!?,” he boomed as he anxiously fine-tuned his necktie. His panic piqued my 20-year-old naive, judgmental mind: “What an insecure baby – no wonder he’s divorced!” Today, faced with dating in midlife, his panic seems all too familiar.
Maybe some men can handle midlife dating with an emotional aplomb, relishing each step of the journey. Perhaps others get by comfortably numb as men are told they should. But I suspect for many, like my pal’s Dad, the angst and insecurity we learn in our youth come screaming back as if they had never left.
For many of us, navigating an alien planet would likely feel more comfortable than a sit-down dinner with a new potential partner. Appreciating each date’s unique initial rules of engagement are essential to making a good first impression, except the rules aren’t written down anywhere, and if you thought you ever even had a clue on those it was likely illusory.
Today, dating apps produce a daily bounty of your next midlife dating crisis with a mere swipe. While the outdated profile pictures, half-truths, alternative facts, and not-so-user-friendly app platforms are certain deterrents, they all pale in comparison to divining the unknowable stage of recovery from traumatic loss your potential match is in. To make matters worse, there’s a very real pressure to reveal not only that you are but why you are divorced, unattached, or perpetually single to essentially a complete stranger lest you be considered dishonest.
Under these inherently uncomfortable, unnatural conditions, intimate connection becomes the oddest of odysseys, akin to a real-life nightmare, creating opportunities for well- or not-so-well-intended shots where you are most vulnerable. Amidst this emotional mind field come concrete matters of alimony arrangements, child-rearing realities of all ages, and all of our non-dating financial obligations pressing in as well. Have we achieved “chemistry” yet? No wonder so many first dates are over a cup of coffee; cheap, brief, and in public, with an easy access exit in case of a clear mismatch so understandably possible.
Which brings us to the worst part of any kind of dating: rejection. “Don’t let it bother you,” is always easier said than done. The fear of being declined is brutal, yet typically pales in comparison to the event itself. The question almost always becomes not if, but when, and are you giving it or getting it? Despite the relentless poundings of pains past, the reality is that the stench of rejection is a necessary and ever-pervading element of dating. Turning someone down can in fact be so painful that you may find an entirely dishonest, “This was fun; let’s do it again,” weaseling its way past your lips. Regardless of the blow rejection can have, remember there are worse fates.
So, what’s a semi-aware, sensitive, male midlife-dater to do who is looking for a relationship? A good place to start is accepting, that, “All of us are much more human than otherwise.” Acknowledging that people don’t really know themselves, have trouble expressing their experience accurately, and are always changing entities, can help us marvel at the miracle that connections happen at all. We are all in the big hot mess that is the human condition together, so at least we are not alone on this existential journey.
Next is accepting that control is an illusion; the surprises will come fast and furious, bring your nimble shoes to this dance.
Check-in with yourself early and often: Are you ready for dating or are the ghosts of relationships past taunting you? Don’t “X”-box your date – if they remind you of your ex because they have two eyes and a nose maybe you aren’t ready to go out there. Are your expectations realistic or are they already premeditated resentments? What kind of partner are you really without the glow from your own self-inflated ray filter? Ouch! Know and own what is currently making you the most vulnerable.
Tenaciously maintaining good manners, grace, and poise, at least helps you keep your dignity, especially on social media, where the pull to be a boor is almost irresistible. Let yourself be a rookie and learn. The first 99 dates are just practice – no pressure. Remember to look at how you are getting along, not whether your date can pass some kind of Baltimore Colts quiz. Be patient; there is no such thing as instant intimacy, especially in midlife.
If you find yourself in great distress, agitated and/or unable to function well over this situation, take a deep breath. If you’re having trouble identifying why you’re struggling, or perhaps a resolution proves itself too elusive, consider professional, therapeutic help. There is no greater fulfillment than love, so take whatever steps you need to enable yourself to find it. Everyone’s journey is different, and no one is without hope.
 Harry Stack Sullivan, MD 2/21/1982 – 01/14/1949
 Diner http://www.imdb.com/title/tt0083833/