If you’re an experienced dater, you’ve probably had your share of heartache. 100hookup member Van Wallach argues that opening up about painful lessons can show someone new that you’re looking for love, not just a good time. (But save the blow-by-blow of your last breakup for your mother.)

After my divorce, I had to readjust to the dating world. The stability of a 12-year marriage vanished into the constant flux of new contacts and opportunities. I found that telling stories about myself—my history, interests, and hopes—was a recurring theme in this strange new land.

Much as in a job interview, the stories we tell on dates are designed to make good first impressions. In fact, so much of this adult dating stuff seems like nothing more than the recitation of preset narratives. Two people make an acquaintance and, as they proceed, start talking. Initially, conversations rarely progress beyond the standard questions posed and reliable answers proffered. If the elusive chemistry exists, the masks slip down so a less polished self may emerge. Then the real connection begins. If the elusive chemistry exists, the masks slip down so a less polished self may emerge. Then the real connection begins.

The masks slipped quickly last spring when I met a woman I’ll call Sandi. From our first encounters on 100hookup and then in person, I sensed something special about her—and, about us. We revealed bits about ourselves that very few others know. I allowed plans for what we could do, what we could be, to form in my mind. That’s what happens when a woman touches the reptilian boy-girl attraction node deep inside my soul.

It didn’t last. Sandi thrashed in a spider-web of complications involving parents and exes that thwarted our relationship, so we constantly took one step forward and two steps back. Finally, she decided to take two steps back and no steps forward. I was abruptly left to thrash on my own. I could take only meager solace from changes she made to her online dating profile, which now read, “Sometimes you meet the right man at the wrong time.”

Months later, the heartache of Sandi remained with me in a surprising way. During 100hookup conversations, I would talk to some degree about my marriage or my nuttier dating adventures (such as separately contacting two women who turned out to be sisters, or the woman who pestered me for confidential files from my employer), but never about Sandi. The whole sequence was so baffling and hurtful, so close to my dreams and expectations of what life could hold.

But, I am finding that heartache carries a functional value. That value emerges in response to questions that singles tend to ask. For my part, I never inquire about women’s dating experiences, online services to which they subscribe, or anything else that crosses into the realm of “none of my business.”

However, some of my dates are curious about these personal and pertinent details. Do I date much? What’s my online personals experience been like?

Indeed, Sandi and I had that type of conversation in our relationship. Strolling along the lakefront one lingering summer afternoon, we talked freely about our pasts. After a deep breath, I told her about a profoundly upsetting episode in my romantic history. I held nothing back from Sandi in telling the story—nothing. We held hands and she responded with great empathy. From those moments in the dappled sunlight, I knew our relationship could be based on a level of true trust and support. But the ice floes of life moved us apart, not closer.

Reluctantly, I moved on. The first time a woman asked me, post-Sandi, whether I had a steady relationship since my day in divorce court, I didn’t know what to say. I finally said I had known different women, made some good friends, but nothing really serious had resulted. Buzz! Wrong answer for this woman, who expressed concern that I may not be serious in my pursuit of romance. These kinds of questions are anything but casual. They aim to sound out whether I’m merely a male hummingbird sipping the nectar of available blossoms or actually serious about this business of romantic cross-pollination.

Afterward, I thought about what she asked and my reply. Treating this as an “it’s none of your business” question may not be the right approach. What was she truly asking? What have I truly felt and experienced? I decided these kinds of questions are anything but casual. They aim to sound out my past and intentions, what I’m seeking, and whether I’m merely a male hummingbird sipping the nectar of available blossoms or actually serious about this business of romantic cross-pollination.

Before long, the issue arose again. This time, I was ready. Combining honesty and discretion, I replied, “Yes, I had something that looked very promising. We really connected. But the timing wasn’t right. It just didn’t work out.”

That basic response may evolve, depending on who’s asking the question and the amount of tequila accompanying the conversation. Sandi and I did have something potentially serious, and I’ll be damned if I’m going to downplay what it meant – what it meant for me, anyway. No, I’m not going to offer my heartfelt confessional to every complete stranger I meet for a drink. But now, if asked, at least I have a narrative that shows I am indeed capable and serious.