The Top 10 Dudes I’ve Dated


It is too often that single girls such as myself become cynical. We tend to focus on the bad dates that we have been subjected to and the bad behavior of the men who have entered and exited our lives. With 2015 upon us, I am choosing to reflect on the great guys I have dated in the past (because there ARE good guys out there) instead of the ones who have truly sucked (at life, at dating, and basically in general). I have compiled a list of the Top 10 Dudes I have dated and encourage all of the single ladies to do the same. I think it is about time that we focus on the positive side of dating instead of the negative. Here is my list of really cool ad interesting dudes that I have had the pleasure of dating (using their nicknames, of course):

10. The “High School Sweetheart” Guy

This guy was great. We dated for two years in high school until he started to become a HUGE drug dealer. While we dated, he was the best 15-year-old boyfriend a girl could ask for. He brought me flowers on anniversaries (or “monthiversaries”) and never once disrespected me. He got into some bad habits, which is why we ended things, but we always stayed in contact. He graced me with the most gracious of breakups and really never broke my heart. Good guy!

9. The “I Wear Khakis” Guy

I am not a khakis kinda girl. I am a native Brooklynite that has only ever dated guys who wear jeans or sweatpants, so the whole idea of wearing khakis to run errands is foreign to me. This guy dressed like every day was a giant frat party, but he was a great guy to date. We had absolutely no spark (on my end, at least), but I dated him because I wanted to do something “out of my element.” He was out of my element for sure. He didn’t cuss and was always politically correct. He was often boring (in my eyes, at least), but we went to plenty of nice dinners and cool fratty parties where I did not fit in. In short, there was no spark, but he was always a gentleman.

8. The “We Should Probably Get Married” Guy

My entire family adored this guy…except for me. We grew up in the same neighborhood, shared a million mutual friends, and came from the same background. None of this mattered, though. No matter how hard I tried, I could not feel anything for this guy. He was totally hot, but he didn’t rile up an excitement in me. His conversation fell flat too often, and dating him tended to feel like a transaction. My mom was hoping I would marry him, so I guess I should take this opportunity to say, “SORRY MA!”

7. The “Asian Leonardo DiCaprio” Guy

Ah, my Asian Leo. I was so tired of people telling me that I always date the same type of guy—New York natives with tattoos, Italian last names, and a fear of commitment. I figured one way to shut everyone up was to date this totally gorgeous Asian guy who reminded me of Leonardo DiCaprio in The Great Gatsby. This guy was red-hot, had a great job, and wanted a relationship as much as I did. Then, on our second date, he decided to ditch me mid-dinner to go to a club with his guy friends. Asian Leo did not make it to date #3. He was, however, great while he lasted.

6. The “He Could Be My Father” Guy

Such fond memories of this one. My older sister set me up with her husband’s single friend who was 14 years my senior. I was 23 when we began dating and he was 37. Despite the fact that I could have totally been his child (if he were on an episode of Teen Mom), we had a great time together and wanted the same things out of a relationship. We were both aiming to find a life partner, not just someone to fill in the gaps of a boring weekend. He was the ultimate gentleman and adored me. Unfortunately, some 23-year-old women have more, um, stamina than some 37 year-old men (do you really need more detail?!). Things with us fizzled out quickly, but he was a great guy.

5. The “Sicilian Love Affair” Guy

Un grande amore! This guy is definitely one of my favorites. I met him when I was five years old on one of my many visits to Sicily with my family. We became instant best friends. Every summer, I went back to Sicily and he would be there patiently waiting for me. After approximately 13 years of this, we decided to take our friendship to the next level. It turns out that he had always loved me and I had always loved him. We were inseparable when physically together and continued to write lengthy, sappy love letters to each other when we were apart (which was basically 10 months out of the year). We carried on this love affair for a little over a year before I decided that I could no longer torture myself by dating a man on a different continent. He was, however, the first man to ignite a romantic spark in my soul, and I could not be more grateful.

4. The “Other Sicilian” Guy

Now that I am thinking of it, summers in Sicily do tend to be quite romantic. I met this guy while ordering a drink at the bar for my American friend who did not speak a lick of Italian. He noticed I was speaking English and attempted to use all of his English vocabulary to impress me. It worked! I spent the next month by his side. We went on beach dates, boat dates, club dates, dinner dates, hiking dates, camping dates, and basically every other date imaginable. I knew that once my plane took off for NYC, he and I would no longer be an item. I was too young to subject myself to a long-distance relationship. He, however, planned to marry me and whisk me away to the Sicilian mountains (in retrospect, this was not such a bad idea). The day of my departure he pulled up to our villa and asked my mother for my hand in marriage. Mom was startled but excited. She was also curious to see how I would react. I was horrified, as this was too much too soon. Can you really know someone in a month? What if he was terrible? What if I married him, moved to the mountains, and had no other contact with human life? I was not ready for the farm life. I didn’t choose the farm life; it was choosing me. Fortunately, I got on the plane quick enough to dodge all of the cows that needed to be milked. All in all, this guy was great and had good intentions. He just moved way too quickly for me.

3. The “Why Don’t You Love Me?” Guy

This guy would have bent over backwards for me if I asked him to do so, but I never let him move out of the friend zone. We attempted dates, but I struggled to take them seriously. For some reason my brain never registered him as a potential mate. He was handsome, charming, and all that jazz, but his efforts to win me were never successful. I do truly think he was and still is an amazing guy, but he was too similar to me. He did not excite or intrigue me. We were (and still are) cut from the same cloth, but what I am looking for is someone to balance me out. I am looking for someone who opens my eyes to new things. Having too much in common actually hindered our potential romance. All in all, any girl who gets this guy is going to be treated like a princess. I truly do hope he finds what he is looking for someday.

2. The “International” Guy

OK, OKCupid, you messed up big time. Why did you match me with a guy who lives on another continent? Universe, why have you done this to me?! Mr. International was within 10 miles of me while on vacation, and OKCupid decided to match me up with him. We shared a 95% compatibility match AND he was gorgeous (WHAT?!). When I opened up his message, I was thinking “Finally!” Instead, Mr. International had already returned to his native stomping grounds. The stars had not aligned for us. I, however, know what I like and decided that I would humor this and not let the distance hinder my interest. Mr. International sparked something in me that perhaps I thought I could not have again after my last breakup. He sparked in me an interest, a zest for life, and a craving for love. Never had I considered jumping on a plane to a foreign country that I had never been to before, especially for a man I had never met. He sparked that in me, though. He sparked in me the sense of urgency to go wherever my heart takes me. We messaged daily, Skyped frequently, and I began to question my sanity for getting knee-deep into what could potentially morph into a long-distance international relationship. To this day, I do believe that if he was here, we would be phenomenal together. Even when I try to date people on this continent, I always think of him and what it could be with us. He would be my #1 choice if I had a choice. Although I have yet to meet him in the flesh and never actually went on a proper date with him, I am hopeful that the stars will align for us one day. Never say never.

1. The “Magician” Guy

This one is a wildcard. He takes the crown for “Most Interesting Date” in my book. I was dragged to a Broadway magic show with my family and somehow ended up conversing with the star of the show. He was tall, super-doofy but well-dressed, decent looking, and funny. We decided to meet for dinner later that week before he took off on tour, and it went well. He was a gentleman, and even when we were eating dinner, he tried to maintain a low profile. He was not showy or self-centered…or so I thought. He said he admired me for not being a “fangirl” and said he wanted a “normal” relationship, but on our second date, the only thing this guy talked about was himself. For HOURS. He gets the #1 spot because he did plenty of corny magic tricks (ta da!) on the first date. He also made me realize that even a man in the spotlight can be intimidated by a strong woman with her own career and life goals. This was a lesson that I feel I needed to learn, and this was a perfect way to learn it. He was not the greatest guy, and I quickly told him to kick rocks (he did not have the magic in him), but he wins this competition because every I doubt any date that follows could include so much magical entertainment. Dinner and a show for the price of one!