50 First Dates: The 10 Best and Worst Gifts We’ve Ever Received from Romantic Partners

Happy Valentine’s Day! Whether you’ve just started dating someone or are in a long-term relationship, there’s a lot of pressure surrounding this time of year and finding the perfect gift. Need inspiration? Here are some of the hits and misses from our anonymous daters.


50 First Dates anonymously chronicles the fun, romantic, wacky, bizarre and downright awful true experiences of dating in Honolulu. Check back weekly for new first-date stories, where to go to woo a boo, tips on where to meet people and more!


“I was blindfolded and whisked away on a car ride. There was fun music blasting on the radio while I asked for (maybe demanded) clues, and our first stop was a shooting range. So scary, but so cool! After a few rounds (not drinks), I was blindfolded again and he drove me to our lunch spot—my favorite food at the time, taquitos supreme and a large cup of iced horchata, haha! After lunch, blindfolded again, he drove us to our next destination … (as he peeled off my blindfold) an ice rink! It had been years since I last ice skated. He popped open the trunk and brought out my old skates. A fun day with a new experience, yummy food (and ice cold horchata), ice skating and my favorite guy next to me.”




“A perfume bottle inscribed with the wrong name.”




“This sounds totally cheesy, but a guy once made me a mixtape CD for Christmas of love songs that reminded him of me. *insert heart eye emoji* Spoiler alert: The relationship didn’t work out, but to this day, one of my favorite love songs is ‘Dreaming of You’ by Selena (the first song on the mixtape). And yes, I still have the CD. A girl can dream.”




“Free ‘message’ coupons (yeah, it was supposed to be massage coupons).”




“Thirteen years ago, my fiancé (now husband) proposed with a $100 ring he bought at a silent auction because it had no bidders. It was huge so I wore it on my thumb. (Thumbs up! We’re getting hitched!) Right after I said ‘yes’ to his proposal, he said he wanted to buy a ring I picked out myself (and spare himself the headache). Secretly, I think he wanted to make sure I agreed to marry him before he invested.”




“Getting NOTHING for five years with the same significant other, and since my birthday is a week away, I also got NOTHING. Hence why he used to be a significant other.”




“I had just met my now-husband, so I didn’t know much about him, namely his practical gift-giving skills. I wouldn’t say it’s the worst gift I ever received, but that Christmas was the first time I held a telescopic baton in my hands. He got it for me for self-defense. Turns out it’s illegal in Hawai‘i because it’s technically a concealed weapon. I did appreciate the thought, though.”




“Someone gave me two shirts from the brand Puppies Make Me Happy, and then someone else gave me a shirt that says, ‘Hold My Beer While I Pet This Dog.’ Yes, I’m obsessed with my dog, and yes, these gifts are awesome (and I still wear them).”




“One of my exes melted down his old wedding band to create a new ‘promise’ ring for me. It was creepy-cool, like carrying around your boyfriend’s ex’s cremated ashes in a locket. After we split, he wanted me to keep the ring. I sold it to a gold shop and donated the sales to a nonprofit for kids. Gold was worth over $1,500 per ounce that year. Someone benefitted from our misfortune.”





“The sweetest guy in the world found out my stuffed toy monkey—given to me on the day I was born—was literally falling apart. One random day we met up with mutual friends and he gave me denim overalls that he had hand sewn for the toy. I didn’t think we were at the gift-giving level of a relationship and was shocked he handed me the gift in front of others. We had only just started something remotely romantic. And when the hell did he measure the silly little monkey? (They fit perfectly!)”

  creepiest gifts


Check out HONOLULU Magazine’s 50 First Dates blog and then send your sweet/sad/stupid/scary/silly first-date story to web@honolulumagazine.com. It’s anonymous so no excuses!