wedding road trip

Day 36: Dr. Jillian

There may be no one cooler in my world than my younger brother Greg. I’ve always admired his entrepreneurial spirit, easygoing demeanor, and extensive group of incredible friends. Thankfully, Greg and his wife Melissa are not selfish either, which means I’ve had the privilege of getting to know their friends on a personal level, making some of them my own over the years. Given that we’re six years apart in age, I find this especially amazing. Earlier in the trip, we met up with his friend and groomsman Adam in Seattle, so it only made sense to meet up with his wife’s friend and bridesmaid Jillian in Chicago.

I have a special attachment to Jillian for several reasons: she’s smart, she’s funny, she’s gorgeous, and she’s wise beyond her years. She also introduced me to one of my favorite websites, Paperback Swap. Every time I see Jillian at Gregamel-oriented events, we end up chatting non-stop. Meeting her in Chicago for brunch felt like a treat I’ve wanted for years: the chance to get to know her one on one.

We met at Orange, a trendy little brunch place in the Lincoln Park area of Chicago. Jillian brought along her live-in boyfriend Ilya, who is part Abercrombie model and part businessman. Okay, so he’s not really a model, but Jillian, girl, you’ve chosen wisely. We jumped into the good stuff right away when Jillian shared with us the story of how she met Ilya back in California. Jillian, who had recently moved to Chicago from Los Angeles, wasn’t so sure about the whole long distance thing, but she found that she couldn’t get Ilya out of her head. After several months of texting, Facebooking, emailing, weekending and talking, Ilya transferred his job to Chicago and they got a place together. At some point during the brunch they also let it slip that they were going ring shopping later in the afternoon, you know, “just to look.” Uh huh.

Communication is paramount to Jillian and Ilya’s relationship. Given that Jillian is going back to school to get her Masters in Marriage and Family Therapy, their relationship is prime testing ground for everything she is going to learn along the way. To be honest, they are miles ahead of many couples, as both Jillian and Ilya are direct communicators who have no problem sharing their own wants and needs.

As for advice, Jillian is convinced that developing strong relationships with each other’s families is the key to success. While both of them live away from their California families, they intend to return to the Golden State when kids come into the picture. Both of them are ecstatic that their families are on board with their relationship, with Ilya commenting, “I think my family loves Jillian more than me.”

We all know how I feel about people expressing strong opinions about what Chris and I want to do with our lives, so I really hesitate as I say this, but… I will anyways…

Dr. Jillian- I think you have a good one here. I can’t wait to see how your relationship grows and changes. Something in my gut just says you’re on to something here…

O Chicago

After a morning of road construction, golden retriever puppies, and the great Dave Davis, we pulled into Oak Park,  Chicago, for the much anticipated reunion with our friends Olivia and Jafer and their three-month-old daughter Camilla.  I say reunion because they moved away from San Francisco in January and haven’t looked back.

For our Bay Area readers who cannot fathom leaving Fog City, let me share this with you: Olivia and Jafer rent a five bedroom house in an inner-ring suburb loaded with Frank Lloyd Wright buildings, a very short walk from shops, movie theaters, and an El station, with the train offering a 15 minute ride to downtown Chicago. It’s as convenient as Noe Valley, but in a bigger city with more culture (and let’s face it, the arts scene in SF is sort of on life support), all for the cost of their old two-bedroom apartment in Burlingame. Makes one think…

Seeing Olivia is extra fun for me, because she’s one of my urban planner friends, so we can talk excitedly about floor-to-area-ratios and streetscape design while Jaime’s eyes glaze over. Even so, over dinner we got to the good stuff: relationship lessons.  My favorite tip came from Jafer, who explained how it’s great to take risks together (moving, kids, investments, trying blowfish sushi, etc.). This idea is coupled with a phrase I admittedly had not heard before “the harder you work the luckier you get.”

For many people, such as Warren Buffett (who is surely reading this website), “work hard and take risks” would not be astounding advice.  However, I’m traditionally a risk-adverse person and have usually just done the “work hard” half of the equation. But Jaime’s been lobbying me to take more leaps of faith – she calls it the magic of believing – that are grounded in preparation and confidence. And I am marrying her in part because she’s very good at setting high goals and fulfilling them. Even so it’s not easy to just change a lifelong behavioral pattern. I’ve been slowly realizing what Olivia and Jafer said so succinctly – take risks together. Jaime isn’t expecting me to jump off the high dive by myself. Which is good… because I’m afraid of heights.