Last year I went to Italy for my best friend’s wedding and ended up sleeping with her husband’s best friend at the reception. I was sure I would never see him again, but he hunted me down the next night and ended up driving me to the airport for my departure the next morning. We connected on Facebook and wrote emails to each other regularly. I decided to return to Italy for two months, and while I was living in Florence our love affair continued and intensified. When it came time for me to leave Italy, I cried uncontrollably all the way to my connection in Paris!  When I got home I confessed my love for him via email. He responded that he also loved me but he wasn’t sure it was in the “same way.” In the year since then we email each other and he occasionally professes his love and how much he misses me, which sends me reeling. He came to visit me in August and we spent almost three weeks together in Colorado and out east. I daydream about moving back to Italy just to see if he is The One. I can’t discern my feelings for him anymore. Am I in love with him or am I in love with our romantic unreal experience? How do I really know if I love this man? — Is That Amore?

OK, I’m about to discuss a short scene from last night’s episode of “Mad Men,” so if you haven’t watch it yet — oh my God, you have to watch it!!! — you may want to stop reading. Are we all good now? Good. Now that we can speak freely, first, how awesome was Joan’s big moment last night when she finally gave Dr. Rape what he had coming? I cheered! And then I rewound and watched it several times over. If you don’t have the show recorded, luckily NYMag.com created an animated GIF.

OK, first of all, let me make it clear that I don’t believe in the concept of “the one.” I think each of us has more like the “top 40” or even “winning 100,” depending on how much ground you cover. But even in a world brimming with possibilities, at some point in our lives most of us have found ourselves infatuated with a guy who was just completely wrong for us. Not that he was necessarily a bad guy—he was just a dude we should’ve relegated to fling territory instead of fooling ourselves into thinking had long-term potential.

Here are a few factors that may give you a case of the stupids…

After five years of hard-core monogamy, my best friend recently put herself back on the dating market. Did she fall out of love? No. Did her (now ex) boyfriend cheat on her? Not quite. Was she afraid of commitment? Not at all. She simply wanted to “see what else was out there.” My gal-pal is a young 23, and this five-year relationship was her first. The problem was, she wasn’t quite sure she wanted it to be her last. It seems to me that we have become more and more wary of sticking to that first love, in fear that the urge to experiment with others will always be in the back of our minds. As my parents’ failed marriage proved to me, happy high school (or college, or grad-school) sweethearts don’t always end up happy life partners. Maybe it's good to do some soul-searching, or spouse-searching, before we settle down. But here’s a perfect example of “damned if you do, damned if you don’t." If we throw away what we have now in hopes that something better—something we haven’t yet experienced—will come along, we might end up regretting it. But if we stay in our first-love comfort zone, we might always wonder. So the question is, should you/would you give up your first love to test the waters? Or in doing so are you throwing something quite valuable, possibly irreplaceable, away?

Earlier this week we posted an essay from a woman who broke her engagement after she realized the traditional signs she relied on to let her know she’d found “The One” had failed. While I’m sure she learned a lot from the experience, I want to save you from a similar painful fate. Forget everything you’ve ever heard about “The One” being your best friend or whatever other nonsense that has been passed down through misinformed generations or stupid magazines. After the jump are the 15 signs that will really tell you if he’s “The One.”

Right now, I’m in the most serious relationship I’ve ever been in; as in, even though I live in New York and he lives in San Francisco, we’ve talked about where and when we could live together—and how soon. He’s met my uncle; I’ve gone to his family’s cabin, and I’m joining them for Thanksgiving. His mom sends me emails, and my grandmother sends me clippings urging him to stop smoking. We talk almost every night and end most calls with “I love you.”