The assignment seemed fun and straightforward enough: with Valentine’s Day nearing, write about how we, as baby boomers and beyond, meet, date and relate to one another. What are the realities, joys, challenges and pitfalls involved in establishing and maintaining relationships among people over 50?

Plowing headfirst into America’s $700-million-plus relationship industry to talk with the experts, I immediately began learning a lot. I learned to hang up as fast as possible when the dating expert you’re interviewing says: “Just come to my free, two-day seminar and I’ll tell you all about it! It’s guaranteed and there are no obligations!” I learned that when you e-mail questions to the doctor in residence at www.LoveologyUniversity.com, you receive answers that would make Hugh Hefner blush. But mostly I learned that it’s next to impossible to interview knowledgeable relationship experts and not compare the information you glean with your own experiences. Do what these experts have to say about partnering jibe with my personal partnering experiences? Do I wish I had spoken with them decades earlier to have avoided all the pitfalls, stupid moves, wrong choices and heartache? After spending time with these professionals, who have forgotten more about dating and romance than I’ve ever known, I made it a point not to ask myself these questions – a point easier proclaimed then carried out.

“You’re never too old to date – you’re never too old to have relationships,” says Sally Landau, a highly regarded Los Angeles relationship and dating coach and operator of www.datingcanbefun.com. “I read a wonderful story recently about a woman in her 90s and a man over 100 deciding to get married – it’s never too late.”

Landau would know – Some 90 percent of her clients are over 50. Most are women, though she says that more and more men are also seeking her services. They come to her, in varying degrees of dismay and confusion, asking why it’s proving so incredibly difficult to meet someone, or why they just can’t seem to find someone who wants the same things out of a relationship, or why every person they choose to date inevitably turns out to be as big a loser as the last person they dated. They come to her frightened by the knowledge that people are living longer – that today’s 50-something divorcee could easily live another 40 years – and they dread the thought of living out those latter years alone.

But more than they fear living the balance of their lives in abject singleness, Landau notes, they dread living the balance of their lives with the wrong person. They want to do it right this time. To each of these clients, Landau asks the same all-important questions she believes lie at the heart of their relationship troubles.

“What do you want out a relationship?” she asks them. “Ask yourself: Who would I be in a relationship? What are my expectations? Are they reasonable? Relationships require a lot of give and take,” she explains. “What are you willing to give?”

“Only when you know exactly what you want can you hope to find what you’re looking for,” Landau says. “Of course, there are those clients – more than you might expect – who, after taking the time to decide what they’re looking for and just how much they’re willing to give, decide they’d just as soon not be in a relationship after all, thank you very much.”

Landau goes on to say that these are people whose friends have been "shoulding" all over them. “They say: ‘You should be out there dating.’ ‘You should get married again.’ They feel put upon. I work with these people and we find, in the end, that they don’t really want a relationship – they like being alone. When I tell them that’s okay, they look at me incredulously. But I say, ‘Really, you don’t have to date – just go live your life.’”

As it happened, that was exactly the frame of mind I myself was in when I met Sharon. It was during a time in my life when the last thing on earth I wanted to do was get serious with anyone. I had just started a new and incredibly demanding editing job at a newspaper, working hellishly long hours that added a good three hours to my hellish commute. I was finally making money – good money – for a chosen profession that can more often than not amount to a vow of poverty. My three-year period of post-divorce devastation that followed my first marriage had faded to the point of seeming like a long-ago bad dream. I was dating again – a lot. In fact, I was dating all the time, and not the kind of “desperately-searching-for-that-missing-half-of-my-soul-to-complete-myself” dating (for which I was previously famous), but rather the “steadily-working-my-way-through-every-department-of-the- paper-looking-for-that-next-someone-to-get-me-through-what-would-otherwise-be-a long-and-lonely-Friday-night” dating that had become the new me.

Sure, I was unhappy – vaguely, almost imperceptibly unhappy – but so what? I was a middle-aged divorcee living in Los Angeles, the world’s largest and most brightly lit playground for middle-aged divorcees. If you’d asked me at the time, I’d have told you I was having the time of my life, a late bloomer who’d finally come into his own.

Then Sharon walked into my life and ruined everything.

“When I work with people, I tell them that whether they like it or not, they have to get to a place where they like themselves,” Landau says. “You have to do more work. I consider you a product or a service. If you’re selling a tangible service, you have to know what it is. You have to know what your boundaries are and how to communicate that – you have to know how to play. A lot of people continue to date and re-date the same type of person because they haven’t figured out that type of person doesn’t work for them – they’re really not clear on what they need.”

I had no earthly idea of the kind of person I needed when I met Sharon, but I was really clear with her exactly what I felt I didn’t need.

“I’m a confirmed bachelor,” I said, sitting across from her on our first date, “and I like it like that. I can’t imagine myself ever living with a woman again. Sure, maybe in a roommate situation, but living with a woman where there’s some romantic entanglement? Been there, done that.”

“Uh-huh,” she said with a wondering look as this charming fellow across from her seemed so confident in saying just what she, or any woman, would want to hear. We were sitting in the patio section of the restaurant, enjoying the sunshine of a perfectly lovely day in May when we had that conversation. By the end of June, we were living together. It sort of just kind of happened. Nothing about me had changed from the day I moved out from last live-in relationship to the day I moved in with Sharon. But somehow I was sure this relationship would be different.

Sharon wasn’t so sure, but then she’d been married twice before whereas I’d been only once. I felt my one horrible marriage experience earned me a black belt in relationships. But come on – her two experiences earned her both a black belt and a license to carry a relationship firearm, which she was perfectly ready pull out to shoot our cohabitation dead if the situation so required. Fortunately, she saw something in me worth keeping – something I had yet to see in myself for the simple reason I hadn’t the foggiest idea of who I was or what I wanted.

“Know thyself!” says Maryanne Comaroto, encapsulating what she describes as the single most important piece of information she gives her relationship-seeking clients. Comaroto is a relationship expert, activist, media personality and author of numerous related books, including “Hindsight: What You Need to Know Before You Drop Your Drawers” (Bridge the Gap Publishing, 2009). She views self-awareness as a key component of happy, long-term partnerships.

“Know who you are,” she says. “Don’t lead with unconscious sexuality – with the brain stem. Really know yourself: How did your childhood shape your beliefs and ideals? What are your values? How can you bring them to a relationship and negotiate them in partnership? The old paradigm of relationships is: ‘What can you do for me?’ The new one is: ‘What can we create together?’”

Comaroto views the stakes in the “know thyself” game as almost apocalyptic in nature. “The old paradigm of viewing the world around us in ‘what’s in it for me?’ terms is not only dooming our relationships before they start, but is also sending ripple effects of unhappiness out into the world that’s literally destroying the planet. I would say we’re in the darkness before the dawn,” she says. “It feels really bad because we’re collapsing the old paradigm. There’s a fever pitch right now that’s so intense because people are in the place where everything’s collapsing and they’re trying to go and back and resuscitate the old way because they don’t know what else to do.”

Leading the charge in collapsing the old paradigm, she says, like soldiers in the vanguard of an army fighting the forces of darkness, is the baby-boomer generation. It was this generation that was first to notice that their parents’ way of viewing relationships just wasn’t working anymore.

“I definitely see a trend among people in their mid-50s and older – a lot of empty-nesters whose kids have gone to college and for whom the children had been keeping the marriage together,” Comaroto says. “This age group was influenced by a pretty strong set of moral values, like you should get married before you have sex. There’s a tendency among them to feel stifled more than others by these old paradigms. When they start dating again, they feel suffocated by this heritage of relationship dos and don’ts.”

Freed from their unhappy marriages now that the chicks have flown, rejecting the stifling values their parents handed down to them, these new entrants to the dating scene are “like children in a candy store,” Comaroto says. “They start grabbing their newfound relationship and sexual freedoms with both hands.” Porn addictions and other forms of sexual dysfunction develop, she adds. “And it doesn’t help that the advent of online dating has provided boomers a seemingly unlimited supply of candy from which to pick and choose.”

Okay. So what happens next?

“What happens when people are overwhelmed by too many choices is we go back to what we know,” Comaroto says. “Oftentimes we end up setting up that same trap for ourselves – we find a lot of baby boomers getting married two or three times in rapid succession, repeating patterns and wondering why they’re still not happy. They thought the new person in their lives would give them what they were looking for,” she continues. “But the common denominator in all these failed relationships is ‘me.’”

It took about three weeks for the “me” in the Sharon-and-David Show to make its debut.

For all my protestations of being a confirmed bachelor utterly uninterested in romantic entanglements, getting hopelessly entangled with Sharon was easy. We were magnetically attracted to each other, shared the same values, and challenged each other’s intellects. Our closest friends would watch us together, chattering like birds and finishing the other’s jokes, and inevitably say” “Oh my God, you guys are perfect for one another!”

While getting entangled was easy, staying entangled, after we’d moved in together and commenced the process of bumping into one another’s boundaries – well, that took work. I broke up with her twice that first year of boundary-testing (she says three times, but what does she know), stomping to the door both times and declaring: “That’s it! I’m leaving!” Both times, I didn’t get 15 feet from the driveway before realizing there was no other place I’d rather be and coming back begging her to forgive me, and both times she had the grace to say: “I’m sorry, did you go somewhere?”

What sent me screaming 15 feet for the hills in the first place wasn’t the big stuff. We didn’t fight over money or fidelity or family. It was the little things – the petty, day-to-day annoyances that separately didn’t matter for anything, but piled up on the resentment scale to a point that I couldn’t bear. Of these pitiful little frustrations, the biggest – for me – was a delusion: I became convinced she was actively and maliciously hiding my stuff.

“Honey, where’s that book I was reading?”

“I have no idea.”

“Well, it didn’t have feet! It didn’t just walk away! You hid it somewhere! Why? Why, for the love of all that’s holy, would you hide my stuff?”

This went on for months, with me increasingly convinced she was gaslighting me, to what dark end I’d yet to uncover. Each day brought some fresh outrage of "stuff shenanigans," until it reached the point where all I had to do was start looking around for something and Sharon would shout, “Damn it, I’m not hiding your stuff!”

I wouldn’t know until later just how close Sharon was coming to pulling the plug on the Sharon-and-David Show. How, during the worst of my tirades, she would look at me while mentally cleaning her licensed relationship firearm just in case.

Comaroto believes the boomer generation is at the head of breaking the paradigm and starting to realize what they’re seeking isn’t outside of themselves. “The lesson learned here is it’s not about finding the perfect partner,” Comaroto says. “It’s about ‘who I am,’ about figuring about ‘who I am and what I want.’ That’s a huge question and relationships seem to be the arena in which the new paradigm battle is fought.”

By looking within themselves, by what she calls "inner viewing," Comaroto says, her clients begin to see that there is no “we” without “me.” They learn relationships are not about partners “siphoning energy from each other,” but rather about creating and following a dynamic of creation – about the emergence of the feminine and the sacred in us all. “We can’t just live on the surface,” she says. “Dropping down to the deepest level of our selves is hard, but it’s paving the way – that’s why this generation is kind of like the sacrificial lamb.”

The reward for all that hard work, she says, is huge. Asked to describe what she sees as the ideal healthy relationship, Comaroto paints a picture of partners who are independent of each other and devoted to the daily practice of personal development and spiritual awareness. “These people understand the distinction between conscious and unconscious behavior,” she says. “They understand the three elements necessary for a relationship to thrive: respect, trust, and being a witness to each other's unfolding to the highest version of who the other person was intended to be. The ultimate partnership is people committed to something greater than themselves and in service to each other. These are the relationships in which people thrive – other people want to be near them, they want what these people have.”

After interviewing Comaroto, I hung up the phone and called to Sharon down the hallway.

“Honey, would you say our relationship is based on respect, trust and witnessing each other’s unfolding to a higher version of ourselves?”

“I don’t know,” she replied. “But could you clean up the dog poop on the side of the house? It’s really starting to stink.”

Exactly, I thought to myself. What does some New Age mystic know about how a real relationship works? It wasn’t until later, while transcribing my notes of our interview from gibberish to readable type, that it dawned me how much truth lay in those words.

What it finally took to break the delusion that Sharon was actively out to get me was incontrovertible proof it was just that – a delusion. Sharon left for a three-week business trip to Boston, and before the first week was out I noticed that somehow, some way, she was still managing to hide my stuff. How does she do that? I asked myself. How fiendishly clever of her…wait, she couldn’t do that. Crap, I’ve lost my mind.

The revelation forced me to reconsider my other brooding resentments toward Sharon. I had constantly accused her of keeping the house either too hot or too cold, saying she controlled the thermostat with the ruthlessness of a Prussian general. Yet, with the general thousands of miles away and the thermostat at my command, the house still seemed too cold for comfort. Maybe it wasn’t her – maybe it was those darn plaster walls, as she’d been saying all along.

It also occurred to me, as I looked out upon a vast sea of dirty dishes and empty food cartons, that maybe her insisting I clean up my messes wasn’t merely due to her obsessive-compulsive nature. It was as close to a spiritual moment as someone as decidedly non-spiritual as I am likely to come, an idea I’d never before considered, either with Sharon or any of my previous relationships: Had it been me all along? And if it were, what was I prepared to do about it? I thought about Sharon and about how the thought of her never failed to make me smile, and realized I was prepared to do anything to keep her.

She returned, and things started getting better – not all at once –, but gradually and steadily better. Two years after telling her I wasn’t interested in romantic entanglements, I asked her to marry me. Six years later, we remain in this grand experiment called a healthy and happy relationship, sharing a life, as Sharon calls it, of “love, laughter and good work,” or what Comaroto would call “respect, trust and witnessing,” or what Landau would call “self-knowledge, boundary-setting and communication.”

So how do baby boomers and beyond date and relate to one another? Very poorly or very well, I learned –depending on how closely we’re willing to look within.

David Silva is an award-winning freelance journalist and regular contributor to “Life After 50.”