How I proposed to my boyfriend with the help of his buddies

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.

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.

Comments on How I proposed to my boyfriend with the help of his buddies

  1. What a lovely, sweet story. It makes me wish I’d popped the question to my FH. Congrats to you both. 🙂

  2. 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!!

  3. 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.

  4. 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.

  5. 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. 😛

    • 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.

  6. I loved this! I kept reading so slow, like that was going to spoil the moment or something. LOL!

  7. 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.

  8. 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.

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