64-Year Old Me Giving Dating Advice to 21-Year Old Me

So many ways to love because we’re all unique.

A couple of months ago I reached my 64th year on the planet. One thing age does is hone what was at one time a somewhat nebulous hodgepodge of advice about life into something far more specific and grounded. Hindsight is, as they say, 20/20. Things in the rearview mirror are often much clearer.

I have lots of such Monday morning quarterbacking advice. Give me a chance and I’ll drone on endlessly about education, careers, the culture of stuff, ethics, faith, and a whole bunch more. That would take a lot of page space were I to do justice to all of that. So, let me confine myself here to a single topic since it was broached just today when a young man asked for advice, dating advice.

Let me caveat everything I’m about to offer as advice as being from “my” perspective. I told the young man the same. These are things I’d want because I’m me, not you. We’re not all replicants of each other. We’re all unique. Completely and totally unique. What we want in life and in dating and relationship partners varies, often dramatically. What you’re about to read is indeed me talking to me. If you glean anything useful from it, which is why I’m committing these words to print here, it’s worth it. Be feel free to reject any or all of it.

The background of today’s exchange was that a young man asked me for my advice about dating and relationships generally. He is, I would guess, in his late 20s, an educated technology professional, gay, kinky, and from what I could tell a nice guy and decent human being.

Again, I’m positioning the advice that follows as me talking to my 21-year old self because as with anyone who’s lived a long life, we always idealize that we would have made better or different decisions if we had known then what we know today. Is that true? Maybe. Maybe not. 21-year old me was a sometimes arrogant, overly confident and stubborn guy.

Hopefully people saw me as nice, smart and generally a good fellow, but I was after all 21. Youth is supposed to look at the world through self-confident and optimistic lenses because it’s our young who are often counted on to bring about positive change. Youth also empowers us with a bravado that’s necessary to punch through some of the crap we deal with in our younger years.

Anyway, I doled out some decent advice if I do say so myself to this young man, caveats included. But it made me step away from that exchange and probe deeper inside myself about what I would have benefitted from hearing at that young age about dating and relationships.

Let me repeat, because it’s important, no one should take this as gospel. I’m sure many reading this will disagree with some or perhaps all of it. But this is how I would ideally want my 21-year old self to approach the sometimes-daunting task of diving into the dating pool.

This is also entirely tainted by my own life experience. As a white, former Catholic now atheist, gay, kinky, polyamorous, sapiosexual, urban-centric, socially engaged, politically active man, among other things, all of that informs my world view and therefore my dating guidelines. Your mileage may vary. In fact, for many of you reading this your mileage likely does vary. I do hope though that a bit of what I say here at least prompts you to think long and hard about your dating and relationship requirements.

Obviously, this is pertinent to those who are single and dating, but I contend it’s vital to those in existing relationships too because it could improve your existing relationship(s) or, as difficult as it might be, help you determine if you should stay in the relationship you’re in currently. Self-reflection is always valuable.

When you meet someone and begin to entertain the idea of dating them, here’s how I’d approach it. (Spoiler alert: I failed miserably at doing some of these things in the past. Live and learn.)

Have conversations that elicit someone’s sense of morality and ethics.

Much of the conversation that takes place during initial dates with a person can be superficial, or at least comprised of mostly the fluffier side of our lives. What movies do you like? Where do you like to eat and what type of food? Where did you go to school? Maybe you toss around a few of the cultural hot topics of the day or you might have an already obvious mutual interest. All that’s great. Do that.

At the same time though, see if you can slip in conversational cues to prompt discussion about some of the meatier aspects of life. How do they feel about civil rights? Do they seem to truly see everyone as equal or not? Do their political leanings blind them to moral or ethical shortcomings? If you’re out at a restaurant or night spot, do they treat the staff kindly and politely?

Try to see past the external or the surface of the conversation and dig deeper. Digging deeper doesn’t mean you have to bring down the conversational tone to something too serious for a fun date. Even being aware of the type of information you’re looking for can alert you more readily to those times when your date is offering up valuable information to help you assess if their moral and ethical compass points in the same direction as yours.

Determine their education level and how much they love learning.

By education level I do not mean formal schooling. Degrees and letters after a name don’t impress me much. I’ve encountered too many intelligent high school graduates and too many intellectually challenged college degree recipients.

Instead, I would focus on their personal education. The liberal arts. World affairs. Good communication and writing skills. History. Philosophy. And even a few hard skills likely to foster a good employment future.

Just as importantly, is their learning ongoing or did it essentially stop when they ended their formal schooling? Do they read, take classes, attend discussion groups, attend conferences, have hobbies they’re deeply engaged in, or otherwise actively try to keep learning throughout their lives?

Couch potatoes in front of television sets abound with little desire to learn anything of substance that can’t be fed to them through passive watching or online surfing. If that’s a life you want, great, but I don’t. I want someone who finds life constantly fascinating, who wants to continually learn and grow intellectually and improve their character. My guess is many people do.

How do they care for their body?

Physicality is important. Sure, having a hot buffed body might be an ideal for many, but what I think is more important is how one views their body. Do they take care of it? Exercise? Eat well? Enjoy walks? Play a sport? Go to a gym? Take yoga classes? Do they try and get plenty of sleep? How much do they indulge in alcohol or substances, if at all? Are they on top of their medical and dental care?

I don’t find the short spurts of gym attendance, the aerobics class they attended for three weeks, or the diet they were on to prepare for an ocean cruise to be all that informative. It’s what they do long-term. How do they take care of themselves ongoing? That’s what matters to me.

Taking care of themselves certainly can improve appearance, but it’s the underlying health and where attention to health falls on their list of priorities that matters most to me.

Are they kinky or not, and how do they view sexuality generally?

My sexuality falls on the rather adventurous side of the spectrum. In short, I’m profoundly kinky and have been my entire adult life. Additionally, I self-identify strongly with not only my personal sexuality, but also with a range of kinky erotic subcultures that form a large chunk of my socialization outlets and friend circles. This is a big deal for me, but might be less so for you.

Sex might not even be a front burner issue for you. Just because I’m highly sexual doesn’t mean others have to be. But most people have some level of sexual life, and being kinky is more common than most realize.

If they’re kinky, are they deeply identified with those sexualities or is their sex life more compartmentalized into only occasional bedroom time? Do they want to live a life during which such kink is always a front and center aspect of a relationship or is it an occasional pastime? Do they run with friends and acquaintances who are part of a connected erotic subculture, or are they more of a lone wolf kinkster?

Being kinky can mean one is into any of countless activities and mindsets. All kinks aren’t equal in people’s minds because we like what we like. Our collective tastes run the gamut sexually. It’s a good idea to determine early on if you and a dating partner might take from the same sections of the erotic smorgasbord table or not.

And kinky or not, how do they view sex? Is it something they proudly embrace or do you sense any shame? Do they rigidly adhere to any particular role position in the sex act or are they open to exploring variations? Are their sexual tastes pretty basic (which is totally fine) or are they open to more?

When someone’s been in a relationship a long time, sex and sexuality can fade in importance, but it’s almost always something newly dating partners need to negotiate.

Speaking of the possibility of sexual interest fading over time, how would you get your sexual needs met if your partner does morph into a less sexual creature, or less sexual with you, or less interested in the kind of sex you like? I know that seems like territory no one wants to discuss, but sometimes reality is a harsh mistress. Self-honesty early on can avoid a lot of heartache and erotic frustration.

Are they into monogamy, open relationships or polyamory, and how do they experience love?

How we love and who we love varies considerably person to person. How one views love impacts everyone in the relationship. This is a big deal. A really big deal.

Find out early if they’re someone for whom monogamy is important or are open relationships or polyamorous options on the table? Try to ferret out not just if they say they like certain relationship styles, but do they have much experience with them. It’s one thing to say you’re open to polyamory for example, but quite another thing to have some time in the trenches navigating such relationships.

Along with money, which I’ll discuss here later, I think this is a top tier issue. When I reflect on times when I or friends have had the most challenging issues with which to contend, this topic and money seem to rise to the top often. It’s important to get as much information about this as early as possible to avoid a clash of love and relationship configuration styles in the future.

How important is money and how do they handle it?

Ask any relationship counselor what topic percolates to the top of many a couple’s troubles and it’s money. Finding out how one views, handles and manages money is important. Really important.

Do they spend beyond their means or are they fairly good at budgeting? Do they keep good records? Do they have a savings and/or investment account, and do they stash money regularly or not? If their employer offers investment plans, do they have any of their money deducted from each paycheck?

While many younger people don’t really think about their future years much, let alone retirement, try to find out if they are at least contemplating how to plan financially for their future.

Do they donate money, of any amount, to nonprofits and charities? Are they generous with their money or do they hoard it even when they have some excess? Check to see if they ever pick up a check when out somewhere. And a big one for me, how do they tip? Perhaps it’s my service industry experience in my youth, but anyone who tips a waiter or bartender under 15% immediately becomes suspect to me and I consider it a potential red flag.

Are their bills paid on time? Have they declared bankruptcy and if so, why?

Money is one of those topics that’s often considered an off the table subject and it shouldn’t be. How much someone makes and how they handle that money is a big deal and it will, I guarantee it, become a lightning rod of contention if there’s a significant disconnect between how you and they view money.

Do they want kids or not?

This is likely always a topic heterosexual or opposite-sex couples of any kind should discuss. Once upon a time this wasn’t a question I’d have considered asking a guy back in the early 1970s when I started dating because same-sex parenthood wasn’t considered even remotely possible at that time. Today though it is quite possible, and this is a huge decision point when dating.

I have many same-sex friends with children and over time my guess is this trend will continue. I’ve never wanted kids and someone wanting kids would have been an absolute deal breaker for me when dating. But everyone isn’t me. Lots of people want children. Many long for the parenting experience. Learn early on if this is the case with someone you’re dating. (I’m inserting a plug here for adopting children who need homes. Wonderful way to become a parent.)

Do they believe in God or not, and if they do are they religious?

I was raised a strict Catholic, eight years of Catholic grammar school included. At a fairly young age I turned my back on it, meandered toward agnosticism for many years, then settled on atheism. How one views the existence of God or not, and particularly one’s affiliation with religion, matters to me a lot.

You might be a person of faith, or not. You might affiliate with a religion, or not. You might attend church services, or not. You might be comfortable being a person of faith or not and dating someone with opposing perspectives, or not. There’s no right answer, but I think such beliefs ultimately do end up mattering inside of relationships. Getting this information up front can be quite useful.

Where and how do they like to live?

Living environments influence a lot about our lives. City. Country. Suburbs. House. Apartment. Rooted firmly or nomadic. Midwest, East Coast, West Coast or South (for Americans reading this). These are all great options, but if two people have different living environment preferences, it could matter going forward.

I’m an urban animal, a city guy, and firmly entrenched in West Coast life. It’s where I thrive most. Someone not on board with that choice might not be a match for me.

What are their political leanings?

There are many who feel this topic should not be part of any dating discussions. I vehemently disagree. I was raised in a household that definitively proclaimed that three topics were off the table for discussions: money, religion (even though I was raised by a devout Catholic), and politics.

I had an amazing father and his upbringing was superb (my birth mother is another matter), but his insistence on not discussing these topics led me to blindly accept Richard Nixon as my candidate of choice at the naïve age of 13, actively campaigning for him. Not having those discussions led me to embrace a far more conservative view of the world in my youth than it turns out aligns with my true moral and ethical center.

This stuff needs to be discussed. I would not date someone who refused to discuss politics. It’s a red flag of monumental proportions for me.

And do they vote? If someone doesn’t vote, I wouldn’t date them. That might seem harsh, but someone who doesn’t vote in my mind doesn’t really care much about their country or the citizens in it. It’s a very self-centered stance. Not voting when one is able to is a clear sign to me of someone entirely disengaged from the welfare of the entire community and country. I need to know such things early on.

The ball’s in your court.

That’s a lot, huh? You’ll notice a lot of things were missing. That probably means I don’t consider them nearly as important as what I’ve written about. Your list of questions and topics might be different than mine. That’s as it should be because we’re different people. But what I do hope you do is give this stuff some thought.

In the early throes of any dating or relationship experience we are naturally overtaken by emotions and biochemistry that can trump (sigh, I used to love to be able to use that word more than I do today) our more rational processes. It shouldn’t ruin any dating experience to simultaneously be aware of assessing where you and a date fall amid these and other important life areas.

A good friend once said something that’s stuck with me forever. “The red flags are not waving you in.” I think it’s a good idea to find those red flags, if any, early on. Take my advice, or ignore it completely, but I do hope you take the time to probe a bit deeper into the substance of a dating partner before migrating to a more codified relationship of any sort.

Happy dating!

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