A couple of years ago, I took myself on a trip. I went to Puerto Rico alone, and while I was there, I had the good fortune of meeting a man who lived on the island. We hiked and went to dinner together, and it was really a bright spot of my first ever solo vacay.
Part of the reason I had decided to go away was because I was weighing something big. Months earlier, my boyfriend had cheated on me with an ex-girlfriend. As a 35-year-old single mom, I had never been through something like that before. The feelings of sadness and betrayal that came with it were awful.
It wasn't long before he came crawling back, wanting a second chance.
I told the man, whom I'll forever call "My Puerto Rico boyfriend," about what had happened and how impossible I felt my choice was. He revealed that he had been cheated on, multiple times, in fact.
"I don't give second chances," he said. He was so firm on it, that I had to question it.
"Really? Never?" I wanted to know.
"Never," he said. "I did once and it just ended up so much worse." I understood that his hard line came from a place of pain, but also learning.
When I got on the plane to go home, I still had no idea what to do. I wished that I could just move on, but I was still in love. After weeks of continuing to see each other, we did end up dating again. Still, what he did to me was always in the back of my mind. The cheating. The lying. I was never really over it. And I'm not sure if it was him, or me, but nothing he ever gave me felt like enough after that. We dated for about six months before I called it off. In the end, I realized that deep down, I had never truly gotten over what he did.
When I reflected back on the past few years, after the end of that relationship I realized that most of my worst heartbreaks stemmed from ignoring red flags. If I had paid attention in the beginning, I wouldn't have fallen in love and could've saved myself a ton of heartbreak.
I started to wonder if all of the grace I was giving was doing me a disservice.
I've never been particularly good at paying attention to red flags, but noticing when people mistreat you right out of the gate is important, or so I'm learning. Even if the disappointment is small, it might be worth it not to look the other way and pretend you don't notice. Because take it from me — someone who has become really good at letting it go — it probably means something worse is on the way.
Maybe I'm learning, or just growing tired of being exhausted by disappointment, but recently, I said goodbye to a man who seemed kind and genuine but was all over the place with his intentions. After a week or two of sweetly sending me voice texts just to tell me he was thinking about me, his communication fell off. Then he stood me up. He lost track of time hanging out with friends and his phone had died, he said. He had a list of excuses, and he apologized pretty profusely. Still, I wasn't sure I wanted to let it go.
From there, my guard was up, and though I did end up seeing him once more, it was mostly for the sake of closure. He continued to be spotty with communication, though he claimed (when we talked) that he was always thinking about me. But after being stood up and waiting outside his house for a half-hour, everything felt off.
At first, I told myself I was being too harsh. But the truth is, that feeling that something isn't right? That's called an instinct.
He made it easy to see that my instinct had been spot on, too. After I said that I was no longer interested in dating him, he acted out. I felt like I was seeing his true colors. It made me certain that I had done the right thing by not simply letting those red flags go. I was just glad that I saw them before I was hooked.
A week later, he sent me a text late at night, asking if I wanted to be friends with benefits. I didn't. When I wrote back that I wasn't interested, he responded that he only asked because it would be easier than finding someone else to sleep with.
"Wow. Don't I feel special," I sent back.
I don't believe that second chances are always bad. But I do realize now that I've been giving them out much too easily. People shouldn't be standing you up or making you feel like you aren't a priority in big ways or small, ever, let alone after a handful of dates. If someone is newly in your life, they should be giving you their very best. If they aren't doing it now, you really shouldn't expect anything better to be coming later.
Dating is not a slot machine, where you keep putting in quarters, patiently, while waiting to hit the jackpot. You aren't paying your dues. You're wasting your own time.
I'm sure I will give second chances out in the future — I can't pretend I won't. But I'm not going to give them away for free. The next time I give a man a second chance, it will be because he's actually earned it.
Everyone makes mistakes, in dating and in life. That much is true. Still, when it comes to choosing potential partners, if someone makes you question who they really are, you might already have the answer.
