Are you too picky in choosing mates? It’s good to ask this question at any age. Explore possible answers to this one, and nine other related questions.
Is it still okay to be picky in your fifties? I think so. But then I’m still single. And I’ll be the first to admit I’m a work-in-progress when it comes to functional intimate relationships. Still, I think I can scatter some seeds of hope, harvested from six years of post-divorce dating. And I do think it matters to this conversation that in all those other ways humans interact—ways that don’t engage prolonged mouth-to-mouth contact—relations with friends and family, with my kids’ teachers, the letter carrier, the super—those are all skipping along quite well. I have a thicket of friendships that needs regular watering, and gets it. And at fifty-four, I’m not devoid of self-awareness—a working romantic partnership does feel within reach. Close enough anyway, for me to share some thoughts—not advice—on dating for the long-term. I toss these questions out with humor and heart, to take to your own heart, or to ball up and toss in the single-stream recycling bin.
Are you being picky or just choosy? It’s a good question to ask, whether you’re deciding on peanut butter or people. Where should you compromise, and where should you hang tough? At the supermarket or on the dating site, there’s a difference between being hyper-critical and just discerning—which are you? I personally like someone with good teeth and well broken-in boots—and arty. But in New York City, those are easy items to check off your shopping list. Apart from these quirks, I don’t really have a type—yet I still seem to harbor some illogical deal-breakers that may not help my chances of finding love.
Take the guy who was allergic to garlic, onions, leeks and pretty much everything else in the allium family. I asked two friends and got two answers. From the one who didn’t cook: “No big deal.” From the one who did: “Next.” But he was a great guy: smart, stable, empathetic and gainfully employed doing meaningful work he loved. And he treated me well. That all counts for a lot. I passed on no-garlic guy because I couldn’t accept that I’d never feel free to slather garlic butter on bread in our someday home.
Is there a workable solution here? As I’ve puzzled losing good men for bad reasons, it’s never helped matters to make mean faces in the bathroom mirror—or worse, when I’ve fallen into that manhole of fearful thinking, shouting at my reflected self: You’ll die alone. I find comfort when I remember that, while we humans share space on Earth for a few revolutions, we all enter and exit this world alone. This is usually enough to pull me out of my funk and into more productive reflection: Yes I bailed, now how valid was my complaint? Have I ever actually shared a bag of garlic knots with someone? Would this be an especially meaningful shared activity? And thinking back to the one before: Did he really have to love David Bowie, or was it enough that he babysat my purse and didn’t hustle me off the dance floor? Before I roll my cart past another good guy, could I take a closer look at the first five ingredients? A friend recently used this question to help her decide between three candidates she’d been dating: If I lock my keys in my car at one a.m., which one is going to show up to help me fish them out?
Are you making excuses for bad behavior? The problem is, historically speaking, I forget to ask myself this question going in, and also to re-ask it regularly, throughout the relationship. While my friends may be drawn to qualities in mates that don’t matter to me, there is one thing we can all agree upon: we want to be treated well. Who doesn’t? The following questions, when asked then answered honestly, might help clarify things: Is he checking in regularly, or do you do most of the reaching out? Does he pay you an occasional, well-timed and authentic compliment? Or does he drop hints that he’s not really looking to be in a relationship? Does he wash your pots? When you turn in at night, is there a fresh glass of water by your side of the bed? Does he ever show up to your place with three ripe avocados and a lime? Taken alone, no single gesture is essential, but all together they add up to this: an appreciation of you.
Is this relationship more fun than work? Does the person you’re seeing plan fun dates? If you’re like me, a single working parent head-of-household, your bandwidth is stretched microfiber thin. You love your kids, but you also look forward to those Saturday night dates. In relationships established on equal footing, combing the weekend calendar of events is a joint effort. I’m always happy to suggest a walk in the park, followed by a stop at a taco truck. I won’t lie though, it feels good when someone comes up with something to do that would never occur to me, but that feels like something I may want to do every Saturday for the rest of my life.
Is this relationship more work than fun? Relationships “require work.” We know this. But how much work are you willing to put in? I’m full of bright ideas to fix other people’s lives. But now, before I push up my sleeves and overdo for others, I’m asking myself: is this person basically together? Do they have friends and take fairly good care of themselves? How bad are their vices? I don’t want to come off as judgy, I for one can’t kick the caffeine habit, not even close, but I don’t think my trenta matcha latte is going to prove too burdensome for someone else. And their idiosyncrasies or indulgences shouldn’t feel too heavy on my back either.
Is he officially de-coupled, or almost there? Where is he at with his ex? Are they at least on civil terms? Are they too close? Ideally, I hope to see signs of a clean, dispassionate break. I once dated someone who had a polaroid of his ex in plain sight, in his bedroom. I still don’t know how I feel about that. Okay, I do. I feel weird about that.
Is he open to trying new things in bed? How willing are these men I’m dating—men pushing sixty or past it— to leave their comfort zones and change up their games between the sheets? When they discover new glitches in their lovemaking—or mine—how enthusiastic are they to explore new paths to mutual pleasuring? Can they lighten up and still find their sexy? Or do they just get defensive and roll towards the wall? Can I lead them along to a sex shop where we’ll take suggestions from some smart, sex-positive consultant, thirty years our junior? And if they aren’t already sold on tantric sex, are they now willing to look into my eyes, share breaths and try the modified lotus position?
How much time do you want to give this? That’s a big one, isn’t it? For me, it’s until I have clarity. And until then, I take it one-date-at-a-time. Despite advancing age, I embrace my relaxed philosophy, even when my shrink doesn’t. He’ll say: “I think we both see the writing on the wall.” Maybe. But I’ve got to play this out. The heart wants what it wants. This is not orthopedic surgery, where sometimes you have to re-break broken bones that had already started to knit together poorly on their own. Doctors do this all the time. They break bones and realign them, so they fuse together straight and strong. But repeated break-ups and make-ups with men have led me more often to mangled relations and hard feelings than to warmth and wellness. Today I’d rather sit in ambiguity, for as long as it takes.
Do you really want to be in a relationship? My son’s barber, a widower whose marriage was unfortunately cut short somewhere between the silver and golden mark, asked me recently: “Are you happy?” In my defense, I rattled off my “list of goods”: “I’m good. My sons are good. My parents are still good—thank God. Things are good with the ex. Work is good. The car is still good. And the weather! Wow! The weather is so good!” The barber waited to respond until I gave him what he wanted. “Oh and I’ve been dating a little.” “Aha! Good! Good!!...” Do I look miserable? I thought. I don’t think so. Sure, on most nights I’d rather spoon a warm body than three wedge pillows, but I still think I’m good. Yes, I’m good where I’m at right now. Which brings me, perhaps, to the most important question: Am I happier being alone today, than I’d be if I were in the wrong relationship? The answer there is yes.
