The advice that follows below emerges from a series of conversations with women who forgot to meet a significant other when they were younger and remain chronically single.
Lest you doubt Penelope’s expertise on, and understanding of, prolonged singlehood, I provide a brief outline of her credentials:
Few people are as good at spending time alone as Penelope. If there were a handicap system for solitude (as there is for golf), Penelope would be a scratch loner. And that’s why it phases me only occasionally that I have spent the last 15 years largely alone. Not lonely, but alone, single, unmarried and whatever other boxes I have to check on tax returns, doctors’ forms, etc.
Being single means my schedule is very easily adjusted. I don't want to get up early on Saturday? Decision-made—I sleep. I can change my mind about what I’m going to eat for dinner seven times and it generates no friction—no one cares how many times I change my mind about these things.
Being single means I’m a better listener than a speaker, because I go to cafes by myself and I eavesdrop.
Being single means I am subjected to less small talk at work. You see, there are fewer safe topics when you are single and work in an environment where you are meant to have grown a spouse at least 10 years ago (if, for no other reason, than to make corporate America easier to run with obvious targets of small talk and networking connections, like kids and schools).
Being single means I haven’t had a proper boyfriend in 15 years, although I will admit to some highly inappropriate situations that I tried stubbornly to fit into the “boyfriend” category, like an obstinate child slamming the circular peg into the square hole insisting the circular peg can be transformed through sheer will.
At this age, boyfriends do not arrive in the neat and tidy packages they used to show up in, with a youthful smile, a promising job and future, and only one ex-girlfriend who was “great” but just came along too soon. Instead, they usually show up bald, with children, ex-spouse(s), maybe even current spouses, addictions, doubts, and even criminal records.
This is why Penelope believes it critical to offer guidance for NYC women who forgot to meet someone when they were young and naïve. Maybe you were too busy climbing a corporate ladder. Maybe it took you 15+ years to heal a wounded heart. Maybe you thought the proper ordering of a life was to try to become president first and THEN find a significant other. Whatever your story, following is some NYC-based advice for women “of a certain age.”
· The Kind Advice of Others. Unless he or she got married in the last 3 years, do NOT listen to the well-intentioned advice of married friends. Chances are they met their spouses/significant others 10+ years ago and any advice they have is just plain stale. Meeting someone at 25 has little to nothing to do with meeting someone when you’re 40+.
Example: A girlfriend told me that if I meet a guy I should pretend he’s the only guy for whom I’ve ever had romantic feelings. Sorry, but if you’re 40 and you tell a guy that, he's going to assume that either you’re a convicted felon who’s just completed a lengthy prison sentence or that you’re an unusually damaged catholic who has been fighting an urge to join a convent the last two decades. He won’t walk away, he will run, very fast (even if his hips have been replaced already).
· Nothing Has Changed. It seems like everything has changed at this point, your waist included. However, nothing has changed. Men are still men and women are still women. Many of the Men Are From Mars principles still apply. He’s probably still a hunter and you, still a gatherer. This may seem inconsistent with the point immediately above—embrace the contradiction.
· Be flexible. After 10+ years of solitude, even an ex-gymnast like Penelope can be inflexible. You’ve probably developed some laudable lifestyles, like daily yoga, no eating after 10pm and no more than two drinks. Be a little flexible, go out and get tipsy one night rather than spending extra time at the gym. He would probably prefer to spend that time with you rather than you spending it fine-tuning your washboard abs. If you’re still hanging out with him in three years, he’ll probably be encouraging you to spend more time hanging on to the remnants of your six pack, so enjoy the time with him now
· Let Him Pay for Dinner. Unless you’re 21 (in which case, why are you reading this?) and he’s a 45+ year old business man, chances are he’s not trying to subjugate you by paying for dinner. He’s trying to be a gentleman, whatever that means in this day and age. Mind you, I said “let him pay,” not “make him pay,” or judge him for not paying. Make a polite gesture to get your wallet from your purse. And if he calls your bluff and let’s you pay, fergodsakes you better have your wallet with you.
· Talking About Money. This is a tough topic and should be approached with great caution. Maybe it was easier 20 years ago when neither of you had any. Or maybe you’re a trust fund brat (TFB) so you knew that until you had 15 years of therapy under your belt, the topic would be off-limits. Money can be deeply symbolic in different ways for different people so tread lightly. Try not to be visibly disappointed when you learn he has no private jet—that just smacks of gold digging. And if you suspect you earn more than he does, don’t insist on paying for everything, unless your real goal is to castrate him.
· Put Snarky Girl Away. It was with pride that I once joined an online chat group called “I speak sarcasm fluently”. Yet, a constant barrage of acerbic wit and well crafted sarcasm, while welcomed in a bar of male colleagues, probably won’t win you many points if you meet a real keeper. It has no doubt behooved you in the workplace to toughen up and show some moxie, but this is not the place to show how tough you are.
· Getting Good At It. At this point you’ve probably been working a while or, if you’re a TFB, you’ve gotten better at working a room or speaking at benefits. In other words, at this point you’ve gotten used to being good at something. Dating is not something one gets “good at” (notable exceptions include Elizabeth Taylor). The goal is not to become an expert but to get good enough to get lucky (no, not that kind of lucky—that’s called “hooking up”)—lucky enough to get to know someone with whom you could spend a meaningful chunk of your life.
This is just the beginning of a multi-part series that Penelope expects to publish over the coming months. Penelope urges you to write in with your comments and questions, either by email (penelope.frost@yahoo.com), on Facebook or on her blog (http://penelopefrost.blogspot.com).
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