Caitlin and Dylan

Where to Propose in Lake Casitas in Ojai, CA

How We Met

It all started 25 years ago…

When Dylan was but a tiny wee thing, his Mom (Kindra) ran a daycare out of their house so she could be home with Dylan. Meanwhile, Meschal and Joe (Caitlin’s parents) happened to find a sitter close to their house for Chris (Caitlin’s brother) to go to everyday while I went to kindergarten… which happened to be Kindra! So, basically, Dylan had been stalking me for the last 25 years leading up to our first date. It all goes a little something like this:

We met on a dating app called “Plenty of Fish”… after about a month of talking I took a break from online dating altogether. When I reactivated my profile a few months later Dylan reached out to me because we had been talking before I went on break. He asked if he could take me on a date instead of just exchanging pleasantries and texts. I agreed to go on a date and even let him come pick me up from my house where I lived with Cassie and Jordan. The first thing he did when he knocked on the front door after I opened it was bent down and pet Izzie… who was about 6 months old at that point. I mean who can resist a puppy?! Honestly though, he was probably trying to distract himself from staring at the giant knee down big black boot on my right leg because I had broken my foot a few weeks earlier… so, here I was about to go on this first date with this guy I just met and I was injured and couldn’t run if I needed to. Good thing for me, he was a gentleman and walked me to the car and opened my door. Off we went…

We went to Downtown Ventura to Taj Cafe. (This is the first time I had ever had Indian food.) He ordered all the delicious things for me to try and I fell in love… with the food. We could not stop talking about everything under the sun. The restaurant eventually kicked us out because they were closed so we continued to talk and walked down to the beach, boot and all. We sat on a bench on the boardwalk talking until past midnight and then we started to notice that there were a lot of people, including children, out and about for it being so late at night. Suddenly, I noticed there were some glimmers on the sand!


Dylan didn’t believe me. He had never seen them before in real life. He had only ever heard the legend of them. I could tell he wanted to go down to the sand and catch them… but I had my boot! I told him he could go down without me. I couldn’t let him miss out on this opportunity to see and catch some of the all elusive grunion! So as he took off down to the sand my FOMO (Fear of Missing Out) set in… so with my boot and all I walked down the stairs and onto the sand where I joined him catching grunion with our bare hands and my boot getting all the sand and saltwater in it.

It was an amazingly great first date and we haven’t looked back since. Shortly there after, we booked our first international flight together to Bali, Indonesia and left on the plane on our 4 month anniversary. Since then we have gone on many adventures and visited many different parts of Mexico, Hawaii, Ireland and Thailand.

Cheers to the rest of our Adventures.



How They Asked

I knew (for way too long) that Caitlin was the person for me so I had to propose.

Step 1 – Obtain her Father’s (Joe) Blessing:

I setup a rendezvous with Joe, to meet at Meschal’s resting place on Friday where he brings her fresh flowers every week. This was the first time I had been nervous aside from meeting him…and 20-30 other family members for the first time at a 4th of July party.

I took two days off of work to work on writing down everything I felt I needed to say and he deserved to hear and then rehearsing it over…and over………and over again. While sitting in the parking lot waiting for Joe (I made sure to be 30 minutes early) I did a few more dry runs.

When he showed up we had the talk, and I got the approval I needed to move forward.

Step 2- Acquire Ring:

I was extremely fortunate in that Caitlin has been very direct in her ring wishes since about month number six of our relationship. So I knew nearly exactly what she wanted. My nosy Uncle Scott (I think he loves her more than he loves me) poked me a few times about the ring and what I was getting. I told him it was all good, I had it all figured out. He then trapped me into a three-way text with his jewelry-aficionado friend.

I sent the friend a link to the ring Caitlin wanted. She gave me some tips on how to shop Jewelers. Following her advice led me to a father-son Jeweler team down in Irvine, and they were amazing! Seeing as Caitlin already knew what she wanted as a ring, since she was so specific on her wants, I setup a day for us to go down to Irvine and meet with the Jeweler to discuss the custom design. This was an incredible experience because he was able to ask questions that Caitlin didn’t even know to consider and they got the ring totally dialed in. We even got 3-d printed samples for Caitlin to fine tune the design to exact her specifications. She never got to see the finished product and she didn’t know when it or the proposal would come…

Step 3 – Figure out how to ask her:

Family is incredibly important to both Caitlin and I. Because of this, and that I had kept everyone waiting for so long, I wanted to do it with as much of the family around as possible – Memorial Day Weekend.

I know Caitlin loves photos, so I needed to figure that out… insert Rob and Nuala (Caitlin’s Aunt and Uncle). I went back and forth with them for weeks to figure out how best to do it and maintain the element of surprise with a professional camera and a video camera sitting there for everyone to see.

We decided that it would be best to do it during the family photo that gets taken at camping every year. This would make it not weird at all to have the cameras out.

This lead to the next item to trouble shoot, how to get Caitlin and I to the front of the photo since the policy has always been short people in the front.

Meschal (Caitlin’s Mom) threw me a bone here! She gave me the excuse to frame the photo this year as a memorial/tribute to her since she passed less than one year prior. Being a memorial photo for her would make it only logical that her household (of giants) was front and center for the photo. To help sell this ruse I asked Caitlin’s Dad and Brother to spread the word to the family so I didn’t appear to have any involvement in it. Joe and Chris toldthe family that the photo would be in memory of Meschal and to be sure to wear a Hawaiian style shirt because she loved Jimmy Buffet and having fun. Nobody could question this – thanks Meschal!

Priority number one was making sure Caitlin was surprised. Priority number two was surprising as many of the family members as possible. So I tried to keep things as quiet as possible and keep everything that happened feeling organic.

Step 4 – How to get some of the people I wanted without tipping her off:

There were several people that would not normally be at the Memorial Day camping trip (my family) but I wanted to be there for the big moment. Luckily for me *wink wink*, Caitlin is INCREDIBLY observant. So this task of slyly coordinating everyone and not giving it away required some creative thought. I worked out story lines with everybody behind the scenes and they played their roles perfectly.

My cousin, Austin, called on my speakerphone as Caitlin and I were driving and said he and his girlfriend Mckenna would be passing through Ventura that weekend and wanted to visit. Caitlin took over the conversation invited him to come camping. This worked out better than I could have hoped! On the day of (though planned weeks in advance), my Aunt Gina made up a story about being on her way home from wine country to Oceanside and wanting to stop by and see Austin on her way.

My Uncle Scott told my mom he and my Aunt Sigrid wanted come, visit her on the long weekend. She said it was fine with her if they didn’t mind coming to the Kearns camp out with her. Just like I thought she would.

Ashley, Caitlin’s friend, usually comes up to visit during the Memorial Day camping trip, but this year there was a scheduling conflict that looked like she wouldn’t be able to come, but she made it happen and was able to text Caitlin about coordinating coming up so it looked like business as usual.

Caitlin’s Aunt, Heather, helped me get Judy (Caitlin’s Maternal Grandmother) there under the guise of being a Memorial for Meschal and thus maintaining the element of surprise for Judy.

Step 5 – Get a Ring Box?:

I had no clue this was even a thing…but apparently, it is. Luckily I found this out two weeks prior to needing it.

I saw ring boxes online and could have bought one and had it in just in time, but that didn’t feel right. You see, prior to our trip to Bali, four months into dating, we decided to DIY leather passport holders to save some money as they were a little over $100 each.

I had a Tandy Leather stamping and carving kit I had gotten years ago as a gift. With all the confidence in the world, I told my new Girlfriend it would be easy and I knew how to do it. That was only half true. I did know how to do it (mostly).

The arduous process entailed: hand-cuting; hand-carving a map of the world with tiny islands included; hand-staining; hand-piercing the holes to thread through; hand-stitching (painfully). Luckily instead of paying somewhere around $100 each it only cost about $300 in supplies and then many hours of labor. But it was a bonding experience that we still laugh about today.

In the spirit of this first project together I decided I could make the silly little ring box. What was there to do besides folding some thin cardboard and gluing some fabric around it? Well, let me tell you. I had to learn how to hand embroider. I had to source materials – this included an impromptu run the fashion district in LA for the right color and quality of velvet and then driving all over Ventura County multiple times to try and locate 1 mm thick cardstock.

Then there was constructing the box. I quickly learned that although the DIY instructions online were nice, the dimensions of my cardstock box kept getting messed up when the fabric was applied so I had to make many little boxes with changing dimensions by as little as 1 mm each time.

I had to take two weeks off of work because the only time I could work on the box in secret was when she was at work. I ended up finishing the box less than 30 minutes before she showed up from work on Friday before we were to go on the annual Memorial Day Kearns camping trip. Phew, that was close!

So, two-weeks of missed work, aggravation, fuel from driving for hours, and about $400 dollars later, I had the ring box!

Step 7 – What am I supposed to say?:

With everything going on in the lead up to the proposal I forgot probably the most important thing I needed….What to say!

Like asking Joe for his blessing, I felt that this proposal warranted more than the simple question, “will you marry me?” I wanted to let her, and the family, know that I understood that in the marriage I was seeking from Caitlin there would be fun and happy moments of course, but there will probably be some hard times as well. That I understand and respect this.

Joe and Chris had to leave the campsite and go into town for an hour or so and joining them gave me the perfect opportunity to go along for the ride and get away from Caitlin’s observant eyes for a decent amount of time. I told Caitlin I was going with them so I could grab her Hawaiin shirt for the family photo since she didn’t have it – thanks again Meschal!

On the trip into town, I stayed in the car the entire time and told Joe and Chris not to talk to me, to act like I wasn’t there. I wrote and re-wrote until I had it dialed in. Then I tried to memorize what to say but realized the paragraphs were too much to memorize in the next 20 minutes. So I recited the bullet points.

Step 6 – “..ask her already..”:

The day came. The people who needed to show up. Joe and Michael (Caitlin’s Uncle) got the champagne ready. Rob and Nuala setup the photo scene. I had my four key bullet points memorized. Chris and Makayla (Caitlin’s niece) had the ring in the ring box. It’s go-time!

Caitlin and Dylan's Engagement in Lake Casitas in Ojai, CA

We set up for the picture and when the entire family was situated I got up and grabbed Caitlin’s hand to lead her out in front of the clan. The first couple of comments rolled off my back easily enough, but after the third or fourth my bullet points went out the window. In all my planning for this moment I should have factored in crowd commentary, but I didn’t. So before getting thrown out of my focus I popped the question. Now, you’re probably wondering what she said….She said, “YES”!!!!!

Marriage Proposal Ideas in Lake Casitas in Ojai, CA


1) I asked her dad for his blessing – he said yes.

2) I decided I wanted to do it at memorial day camp out with her massive family and some of mine. Her mother helped in giving me the excuse of a memorial photo to bring our tall selves to the front of the family photo.

3) Caitlin’s Aunt and Uncle photographed and videoed.

4) Caitlin and I met a Jeweler who reviewed and custom-designed it – gave us a CAD file – then made 3-d printed copies – we finalized the design and details – then he crafted the most perfect ring for Caitlin.

5) I spent two-weeks and approximately $400 hand- making a ring box out of velvet and 1 mm (very important) card stock.

6) I proposed. I got to include Meschal in the proposal. Everyone was surprised, with the exception of the 7 or 8 who helped me. Nary a dry eye in the heap. Tears of joy were spilled by many.

7) Now we are getting married!