Figuring out how to handle the money thing is one of the biggest decisions Chris and I will have to make before we attach the ball and chain. Not surprisingly, most of the couples we’ve met up with have combined all of their duckets, preferring to work on a budget and all that shizat as a team. And while I don’t disdain this approach, I must say it’s not where we’re leaning.

Let’s just get something out in the open right now: neither Chris nor I are high-rolling, house-owning, swimming-in-money kinda kids. While we like to stay in hotels like the W and travel to exotic locations like Ephrata, Washington, we’re counting our cash like everyone else. Even if we become the Gatsbys of 2009, we don’t really feel like dropping all of our coin in the same money pot. It just doesn’t sound like a hell of a lot of fun. For example, I imagine the following conversation happening soon after bank account co-mingling:

Chris: Jaime, I bought you this lovely platinum bracelet from Tiffany!
Jaime: Why thank you darling! I couldn’t help but notice that $1,000 deduction on our online banking account yesterday! How thoughtful of you!
Chris: Smooches, did you really spend $4.50 on tampons yesterday? I saw they were two for one at Walgreen’s on Sunday. Tsk, tsk!

So instead of going the traditional route, we’re going to keep our own accounts and have financial summits on a quarterly basis. We’ll chat about how the past quarter has been, going over where we’re at with our current paychecks, and agree on how much we’ll each pay into the common pot for the next quarter. We’ll score a joint account to cover everyday/rent expenses and we’ll both sign up for a percentage that we’ll donate to a team savings account. The rest is ours to play with and spend on each other as we please.

Of course, we’re open to suggestions. Have at it- I’m sure you’ve got your own thing going on that works for you. Feel free to share it!

Obviously I jest, but we did have a few moments of terror on the way into town, thanks to Independence Pass. For anyone scared of roller coasters, heights, or death, I recommend skipping this route and taking the long way. I was driving, so Jaime cringed as I gingerly steered Roxy around hairpin turns and bottomless chasms, culminating in a 12,000 foot crossing of the Continental Divide. The road isn’t so much a pass as a route up and over a mountain.

We arrived in Aspen as Chris and Krystal were finishing their work days. They promptly took us and a sixer of Blue Moon out to the Maroon Bells, where we traipsed mountain meadows while their dog Rosie ran around at approximately 200 MPH. This was followed by dinner at the Woody Creek Tavern, an old Hunter S. Thompson hangout, and conversation back at their beautiful townhouse in Basalt. Yes, we liked Aspen.

One piece of marital advice from Krystal & Chris is that if all else fails, get a dog. I’m paraphrasing, but the basic gist is that a dog can provide activity, conversation, and all types of mutual experience bonding that you will not get from TV, jogging, or a hamster. The background is that on a drunken whim several years ago, Krystal adopted a stray which has become The World’s Most Awesome Dog, aka Rosie. I first met Rosie two and a half years ago and immediately threatened to dognap her, and still intend to. Inside, she sits quietly on her bed or on my feet, and is so well behaved they can take her to work where she dozes all day. Outside, Rosie takes off at cheetah-like speeds, chasing things like snowmobiles.

So, a dog can spark your relationship in interesting ways, especially if you live near the Great Outdoors and get a dog larger than a purse but smaller than a pickup truck. Sadly, Jaime and I passed on an opportunity to get a golden retriever puppy in Chicago (bad timing), but if we get tired of each other, we’ll swing by Aspen when Chris and Krystal aren’t home and pick up the solution.

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…

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.

For the record, Ulla and Keith are not doing your run of the mill wedding – they have a five-city, three country extravaganza planned. Admittedly, they are from Germany (her), Canada (him) and live in the US, so a single location would have been tough… unless they got married in O’Hare Airport. Hmm…

Keith shared with us a cautionary tale of a past engagement of his that went awry. The story was one of those crazy “I can’t believe that actually happened to you” situations that left Keith burned for several years. But nothing like the magic (and sanity) of Ulla to bring him back to the place where love (and marriage) are possible.

Ulla imparted one key price of perspective – the Buddhist idea of accepting yourself. As I can best recollect, the concept is that before you can truly give yourself to someone else, and accept them, is that you need to accept yourself for who you are. I’ve got to admit I might not be there yet, since there are many things I’d like to improve about myself, but there’s something powerful about the idea.

Josh is the oldest of the cousins and tends to be ahead of the rest of us with marriage, grad school, and children. I even sort of followed him career-wise (he’s a landscape architect, and I’m an urban planner). I’m happy to travel in his wake, since he’s got a solid relationship with Kris and an amazing child in Alexander.

Josh and Kris shared a lot of sound relationship advice with us, but for the purposes of this blog, let’s talk about raising children. We’ve seen a lot of different arrangements of childraising on this journey, and have no definitive judgments on right or wrong – we’re still learning. But we must say that Alexander seems like an exceptional outcome. He is three years old and the first thing he does when he walks in the house is put away his shoes. I am 34 and still have not learned how to do this. He also built a fort out of paper towel rolls, and then promptly put them all away. According to Josh, Alexander came up with the idea himself and brought all of the recyclable paper towels up from the basement without assistance. We couldn’t figure out exactly how Josh and Kris made this happen, but it might be because they treat him respectfully, sort of like a fellow adult (no, he’s not allowed to drink beer or watch HBO).

Sigh. It would be great to get some of that mojo bottled.

They had a few other insights on love and happiness. In a marriage, learn to accept one another’s differences. Wendy accepts that James sometimes likes to wander around with no specific direction, while James is okay with the fact that Wendy includes shopping as one of her hobbies. Along that front, James works some serious Wall Street hours (think, past midnight times seven days a week), which could lead Wendy to wonder whether he’s really in the office, or if he’s actually at the Off Track Betting parlor. But Wendy doesn’t see the value in questioning whether James is downgrading the bond ratings of companies or betting on Seabiscuit – she can either trust him or not.

On finances, they’ve taken turns being the breadwinner, first Wendy when James was in grad school and now James, though Wendy does work a full-time job. (Note: Wendy mentioned that she may need to put in some overtime to cover than Chanel purse she’s been craving.)

The final thing I learned is not related to marriage. In Grand Theft Auto, when you crash a car too much and it starts to smoke, get out right away as it’s about to blow up. Hopefully that information won’t be relevant on our Wedding Road Trip with Roxy.