How I proposed to my boyfriend with the help of his buddies #Friends & Family Advice#proposing Updated Oct 12 2015 (Posted Jan 5 2011) Guest post by Sarah Offbeat bride reader Sarah, shared with us this cute story about how, with the help of a some good friends and a top-secret plan, she popped the question to her man. Sarah and Kunal -- all fiance'd up. I know this has been covered before on Offbeat Bride, but it's a topic that is dear to me, and one that I found tricky to prepare for. Namely, proposing to my boyfriend. Long story short — my dude (Kunal) and I have been together for eight years. The last few of which I kept slamming down the idea of getting married and creating a long-term time line that included me going back to school and getting more degrees. But, a switch flipped in my head this past summer and I was suddenly ready to marry this dude and let him know I was ready to spend the rest of my life with him. I'm not the type of girl who would pick out a ring, then give someone a time frame and tell them to ask me to marry them. I'm the kind of person who believes I can do some things better than other people. So, I called by dude's best friend and told him about how I wanted to pop the proverbial question. The two of us came up with a rough plan, and then I had three weeks to pull it off. (I might be awesome at planning surprises, but I am not awesome at keeping them a secret. My time line needed to be short.) This is where it became hard… …the role reversal seemed to come with less celebration than the standard boy-asks-girl scenario. … Just because I was asking didn't mean I didn't want an awesome memory. Related Post 5 ways NOT to announce your engagement on social media (in GIFs) It's the start of the holiday season. You're full of tryptophan and ready for a nap. OR you're totally celebrating your freshly diamond-ed finger because... Read more I scoured the internet for suggestions on how to propose to a guy. I tried to figure out what "object" I should present to him when I asked. I also just wanted some general advice. I felt confident he would say yes (spoiler: he did), but I still wanted help. I'm a researcher, so it felt necessary to do research. And, let me tell you, resources were hard to come buy. What also interested me was that the role reversal seemed to come with less celebration than the standard boy-asks-girl scenario. In my opinion, just because I was asking didn't mean I didn't want an awesome memory. I wanted to find some place awesome to make the ask, but I had a hard time coming up with one in Chicago, where we live. Ultimately, I decided on New York City — our favorite place in the world, and home to one of our very best friends. I bought two plane tickets and a few nights in a hotel and kept hush about it. Then I sent an email to my guy's younger brother to get his insight and blessing (when I pressed "send" on that email, I thought I would pass out). But, each time I sent the, "I'm going to propose to Kunal" email, I received the greatest, most thoughtful responses from everyone! Each of his friends was incredibly excited and responded positively each time I asked for advice or thoughts or freaked out over not being able to find a really nice watch to present during my ask. In fact, the first friend that I told offered to fly to New York for the weekend to celebrate with us, and Kunal's little brother offered to take the red eye from San Francisco to do the same. Cutting to the chase… the day before we were to leave, I surprised Kunal with our last-minute trip to New York. I cloaked the reasoning under school starting soon (I'm a university librarian) and wanting to take a trip out of dodge with him, before the kiddos came back. Once in New York, one of Kunal's friends hid in the bushes at City Hall park with a camera so that he could shoot the event and then pop out with a "surprise!" This particular friend was the greatest sport — he sat in the bushes, in a dark park (it was midnight!), in New York, for forty-five minutes waiting for us to show up. After he found his spot, he texted me the exact bench where we should sit, so that he could get the best picture. Never having actually been to this park, and being incredibly nervous, I couldn't navigate correctly and we ended up sitting exactly two feet from where he was perched. After he heard the official "yes," he snapped a picture and we both saw a light come from the bushes. When he popped out, Kunal was so freaked out and surprised, every picture we have of the two of us, for about fifteen minutes after that, we look so red-faced and nervous. I didn't get Kunal a ring or watch, as originally planned. I couldn't find one I really, truly liked. Through a brainstorming session with our very best New York friend (who is now my Guy of Honor), I ended up getting him what we deemed the "Ultimate Dude Collection." He received a tie bar, cuff links, and a money clip. Ultimately. I wanted to convey "wear these things on our wedding day." The next morning, when the whole gang met up for brunch, Kunal's little brother suddenly walked down the block — fresh off a plane from San Francisco — ready to eat. We spent the rest of the weekend walking around New York, taking pictures, and drinking and eating great food. The surprises were so well organized and so pleasantly unexpected — being the asker and not the asked was so very worth it. Guest post written by Sarah Sarah is a reader and runner who lives in Chicago with her fiance and two pups. She hopes one day to change the way girls live in the world. http://www.sarahandkunal.com PREVIOUS Tiffany & Nick's hipster Bavarian wedding NEXT An adorable mid-summer wedding to warm your mid-winter day Show/Hide comments [ 22 ] What a lovely, sweet story. It makes me wish I'd popped the question to my FH. Congrats to you both. 🙂 Reply What an awesome story! I love it! Congrats. 🙂 Reply I just let out a huge "HA" when I read the part about him taking the picture and jumping out of the bushes. I can just imagine it was fantastic!! What a great story!! Reply yeah!! Reply Cool idea. We've had a lot of our customers give rings to guys as well, but your idea is cool. Generally they'll get them engraved with a message in or on them.. But I definately liked your idea. Reply I don't know if its all the mushy wedding hoopla I'm involved in right now getting to me lol but this made me tear up and I'm not the crying kind. Very sweet and that you flew his brother in must have been a great surprise as well. I hope you both have a wonderful wedding and most importantly a happy, blessed life together. Reply made me tear up too, it's a beautiful story! 🙂 Reply haha, I love this story! Also, as a cynical New Yorker, I can't believe your buddy didn't get mugged or arrested or fall into a puddle of hobo pee while hiding in the bushes. 😛 Reply Shorty J, as the gentleman who hid in the bushes for those 45 minutes, I can tell you that the rest of the night I was concerned that the itching sensation on my face was the product of poison ivy, but thankfully it appears to have been nothing other than perhaps the hives of excitement. Can't rule out hobo pee though. Reply I loved this! I kept reading so slow, like that was going to spoil the moment or something. LOL! Reply Good for you! I must admit. I am receiving a library science degree and did a lot of research ahead of time before popping the question to my dude. I agree that there aren't many resources available for women looking to set up a surprise proposal. I wrote a poem as a present and asked him Christmas Day as my gift to myself. I also bought him a ring. Reply Awwww….. amazing! What's even better is that I know this couple used to be from where I'm currently living and I went to some of the most amazing house shows in their basement, over five years ago! It's like, double inspiration. Reply I love this! Those house shows are some of my favorite memories, too! Reply Love it!! I especially enjoyed when the friend took the picture … IN THE BUSH … then popped out. That is just magic and amazing! LOL Reply Fantastic!! I love this: "I'm not the type of girl who would pick out a ring, then give someone a time frame and tell them to ask me to marry them. I'm the kind of person who believes I can do some things better than other people." High five, empowered woman! Reply I asked my fiance too, and I hate that whenever I say I'm engaged, people asked how he proposed to me! It's great to hear another girl's story, I wish more girls would ask. Reply I love this so much! I wish more women were like you. And your story is adorable. I just love everything about it. It made my day. Reply I too proposed to my now husband. I actually proposed in Millenium park at the fountains with a book all about the reasons i love him with the proposal at the end of the book. Yay for girls who take care of business! Reply I know this is a guy proposing in it, but I couldn't help but link this in… it's THE most amazingly cute proposal I've ever ever seen =D Reply How cute! I also proposed to my husband since it was a leap year. I bought a ring for him with a geeky mobius design, and was planning to wait until leap day, but I couldnt wait that long and proposed the day I bought it! Reply Thank you so much for writing this post (old as it is)! I too have been "researching" and coming up short. I wanted something he can wear daily and glance at to get excited about the engagement, but men's rings are such a contentious fashion question, and my s/o already has a watch. And I love cufflinks, but he never wears French cuff shirts! I've been totally stumped, though, so I love your/his friend's idea of the three gifts being intended for use on the wedding — it may not be something he can wear every day but it's still special and keepsake-y and not just a random father's-day-style present. Reply Hey there! I just stumbled on your comment. Depending if you've already done the asking, I will say that Kunal says if I hadn't had any actual object to present to him, he still would have said yes. I had this weird idea that I needed something "real" otherwise he might have said no, taking that as his cue to then ask me (it made sense at the time). The second idea I had had, which is very practical and particular to me, was to buy him a Roth IRA. On the outset it doesn't sound very romantic, but if an engagement ring is supposed to show some symbol of someone's investment in their partner's future, a Roth IRA is explicitly just that. Plus, it's nothing but useful. You're right, those cufflinks were worn on our wedding day, but I don't think they've come back out since then. But that's also totally o.k. 🙂 Reply Join the conversation Cancel Reply Your email address will not be published. Required fields are marked *Comment Save my name, email, and website in this browser for the next time I comment. Sign me up for your offbeat awesomeness newsletter! No-drama comment policy Part of what makes the Offbeat Empire different is our commitment to civil, constructive commenting. Make sure you're familiar with our no-drama comment policy. 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