When it comes time to discuss love and relationships with my daughters, I aim to delve deeper than just the basics. I want to instill in them values of confidence, intuition, and authenticity. My goal is to spare them from learning life’s lessons the hard way, though I understand that may be a tall order.
Reflecting on my own awkward romantic history, I don’t feel particularly ashamed but rather wish I could give my younger self a firm wake-up call.
Post-college was an exhilarating time for dating; the world felt vibrant and full of possibilities, with people eager to connect. I often found myself meeting new guys, whether it was at a late-night bar or through mutual friends. One particular evening, I met Alex, a finance guy whose charm was hard to resist.
When I first noticed him, he had already shed his jacket and loosened his tie, his hair falling casually over his forehead. He asked for my number at 3 a.m. and, by 11 a.m. the next day, had already set up a dinner date.
For our outing, I chose an outfit that I thought struck the right balance between conservative and flirtatious: a long-sleeved top paired with a very short black skirt and towering heels. At barely 5-foot-2, I often relied on high platforms to boost my confidence. In hindsight, I resembled a slightly overdressed performer.
Alex took me to a quaint Italian spot in the East Village. Our conversation was stilted, but I still found him attractive. After a few glasses of wine to ease the tension, I excused myself to the restroom, which was located at the bottom of a treacherous staircase.
In my tipsy state and precarious heels, I should have grabbed the railing for support. Instead, I clutched my purse. Before I knew it, one heel slipped, and I tumbled down the stairs, landing hard on my behind. The pain was sharp, and I could feel tears welling in my eyes as I gingerly stood up, half-expecting my backside to be a colorful array of bruises.
When I returned to the table, I opted for silence about my mishap. The present-day me would’ve laughed about it, using the moment to lighten the mood and bond with Alex. But back then, I was too focused on maintaining a façade of coolness, unwilling to show any vulnerability.
Given that we hardly knew each other, it seemed entirely logical to head back to his apartment for an intimate encounter. The experience was merely okay, but things took a turn when Alex decided to incorporate some playful spanking into the mix—right on the fresh bruise I had just acquired.
It’s astonishing that I didn’t stop him or even protest. I allowed this near-stranger to inflict pain on me. He didn’t know my story; I barely knew my own.
Eventually, I managed to shift positions, which spared me further discomfort. The bruise healed before our second date, but our relationship fizzled out after three months—an impressive duration for not showing one’s true self. Ironically, one of the moments I cherished about Alex was when he ruined dinner by over-salting our meal. I embraced his flaws while hiding my own.
Now that I’m a mom in my 40s, I feel a mix of protectiveness and pity for that 24-year-old girl who lacked the self-assurance to stand up for herself, even in vulnerable moments. I understand that my daughters will need to carve their own paths, but if I could prevent them from experiencing my missteps, I would. If only there was a way to share this tale without the more embarrassing details.
Oh, I see your point—by publishing this online, I’ve essentially told them already. But given how busy the internet is, they might have to search for my name alongside “embarrassing” and “sex” to find it.
So, future daughters, just know that I was once young too, and this is what I’ve learned: Your well-being is more important than your image. Have confidence. Trust your instincts. Stay true to who you are. And for goodness’ sake, hold onto the railing when going down stairs!
Summary
The author reflects on her past dating experiences, particularly a memorable date that highlighted her insecurities and mistakes. She emphasizes the importance of self-confidence, intuition, and authenticity to her future daughters, hoping to impart wisdom that could help them avoid similar pitfalls.