“The Hardest I Worked For Love”

How far would you go to get a new relationship off the ground? Be inspired by these true tales of grand gestures.

By Chelsea Kaplan

et’s face it: Sometimes, you have to work hard for a relationship to flourish. Listen to these single people share their stories. They know it takes more than a bouquet of roses or a home-cooked meal to make romance a reality. Here’s how they helped love along.

Aye, aye, sailor!
“Jim, my boyfriend, was a huge sailing fan when we met—he owned a 40-foot sailboat and wanted to do nothing but sail it all day long. I grew up in an urban area and never even
“I packed up my boots and moved to the big city.”
learned how to swim, much less sail! Because I couldn’t swim, I was terrified to go out on that boat, which was almost the end of our relationship (as you can imagine). To surprise him one Valentine’s Day, I secretly signed up for 10 weeks of swimming lessons at my local YMCA. Even though I had private lessons, I was surrounded by all of these kids getting group lessons, which was pretty humiliating considering I was 35. Learning to swim was actually a lot harder than I thought, but I’m so glad I did it. Jim was so surprised—and happy! Spending time on the boat was no longer an issue for me, and I finally got to enjoy all kinds of adventures—including evening skinny dips with Jim! We’re still together today and things are going — pun intended — swimmingly.”
—Ronna, 38, New Haven, CT

The language of love
“I was born and raised in New Jersey, but I fell in love with Fatih, who is Turkish. After dating for about a year, we planned a trip to Turkey so I could meet his family, none of whom spoke English. I spent three months taking lessons in Turkish. It was extremely hard learning this new language so late in life, but I stuck with it, keeping in mind that I would get to know his family better and strengthen our relationship. Plus, I would learn more about Fatih and his culture. I certainly wasn’t fluent when the lessons were over, but I was a big hit during the visit and was definitely able to get to know his family well beyond smiles and nods—and even learned from his mother the secrets to cooking Fatih’s favorite traditional Turkish dishes. We just got married in June—in a ceremony that was conducted in both Turkish and English, much of which I helped write!”
—Maureen, 34, Ridgewood, NJ

(Facial) hair today, gone tomorrow
“My beard was my signature. I’d had it for 25 years. Soon after meeting Diane — who I just knew was my soul mate — she told me that it was too scratchy when we kissed and asked if I’d shave it off. I thought about if for a couple of weeks, and even though everyone I told was horrified, I did it for her. It was almost like losing a good friend. I looked completely different, and it took me a while to look in the mirror and see ‘me,’ but eventually I did. It ended up being a win-win situation—Diane’s face no longer got rubbed raw when we kissed, and as a result, we kissed a whole lot more. We’ve been together for about a year now and are still kissing happily.”
—Ian, 47, Walnut Creek, CA

Ink be gone!
“I had a tattoo of my ex’s name on my ankle, and, understandably, it really bothered my current boyfriend. I knew in order for our relationship to continue, I had to have it removed. It was the longest, most painful process you can imagine. Not only did it take nearly five excruciating procedures, but each removal treatment was seriously expensive. In the end, it was the right decision—a few months after getting it removed, he proposed.”
—Angelique, 24, Bayside, NY

New York state of mind
“I grew up in rural Alabama and lived there my entire life. I love fishing, the warm weather, the hospitality… there’s no place I’d ever rather live. I met Tricia, a New Yorker, online, and after about six months of corresponding, we finally met face-to-face in the big city. I hated it; it was too busy, too crowded and too loud. We dated long-distance for a while but soon knew we had to live in the same town. I wasn’t ready to lose her, but I knew
“I gave up my favorite food for my girl…”
I would have to be the one to move because her job had to be in Manhattan. The thought of living in the city was my worst nightmare, but she was my dream girl, so I packed up my boots and hat and moved to New York. I still struggle with the noise and the cold weather, but seeing her every day sure has made it worth it.”
—Chuck, 32, New York, NY

Dog-gone it
“About six weeks before meeting my boyfriend, Gavin, I had gotten a new golden retriever puppy. Unfortunately, Gavin was extremely allergic to the dog—so much so that even hugging me would make him itch, just from the dog hair clinging to me. Eventually, I had to choose between the two, and it was really tough. I sent the dog to live with my sister and her family about an hour away. I would visit the dog at least once a week while still seeing Gavin. I felt like I had two boyfriends that I had to spend time with! It was pretty exhausting, but I couldn’t give up either. Luckily my sister’s family loved the dog, and Gavin and I were able to spend itch-free time together. Things worked out really well: He and I are now married, and I see the dog often, because my sister recently moved to the same town where we live!”
—Ellen, 30, St. Louis, MO

Movin’ on up
“Shortly after meeting Abby, she was scheduled to move to a new apartment. Wanting to help her out and show her I was a nice guy, I offered to help. What I didn’t know was that she lived in a fifth-floor walk-up! I spent all day with her brother hauling her furniture up and down narrow flights of stairs—in the middle of July. I think I sweated off about 10 pounds that day between the exertion and the heat. But Abby and her brother were impressed with my dedication that day, as they should have been! I recently moved in with her, but if we ever move from this apartment, I’m hiring a moving company!”
—Brian, 25, New York, NY

Diet try-it
“Before meeting Olivia, I was all about eating meat—steak, burgers, you name it. Problem was, Olivia was a vegetarian. She was also unlike any other girl I’d ever met, so I decided to try and give up my favorite food for her. The first few months were really hard; I think I even went through meat withdrawal! Eventually, I got over my desire for it. And ultimately, the sacrifice sure was worth it; we’ve been married for almost a year, and I’m still a vegetarian.”
—Greg, 28, Boston, MA

A Giant effort
“Even though we live in Utah, my boyfriend Derek is the world’s biggest New York Giants fan, despite never having seen a game live. To surprise him for his birthday, I booked plane tickets to New York, thinking that getting Giants tickets and a hotel room would be a snap. As it turned out, I chose the same weekend as the New York Marathon, and the entire city was booked. I spent nearly every day of the next few months calling hotels hoping for a cancellation. I finally got one. I also discovered that Giants seats are nearly impossible to procure unless you have season tickets. I bid on 27 eBay auctions before winning—and I paid an arm and a leg. I never told Derek how long it took, or how hard I worked to make the weekend happen, but he was thrilled.”
—Tiffany, 26, Provo, UT

Wax on, wax off
“I had been dating Fran for a couple of months before we planned a beach trip together. We had only dated in the winter, and she’d never seen me with my shirt off. I was worried that she’d be turned off by my hairy back… and I really wanted to make a good impression and gear up to taking things to a more romantic level. So I decided to get waxed before our trip. It hurt like nothing I ever felt before! I was red and in pain for an entire day. I did, however, show up for our vacation with a back as smooth as a baby’s bottom — and didn’t get the usual “Whoa, you’re hairy!” reaction I usually encounter — so it was well worth it. And it made me more confident about getting closer…”
—Jonah, 27, Hoboken, NJ

Chelsea Kaplan is deputy editor at Her blog, “I’m Somebody’s Mother?” can be found at
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