photo: alykat

I’ve always had a pretty laisser-faire approach to calculating “my share” of financial transactions with friends and family. It stems from my previously mentioned commie streak — instead of allocating shares of bills dead equally, I’m inclined to let the person of the most means shoulder a larger share. Throughout most of my 20s, that person was almost always me.

Not, I hasten to add, that I was swimming in cash. My life is a very distant cry from The Hills or NYC Prep , where a typical afternoon out means dropping the kind of money that would keep me in rentmortgage payments for three months. But I started working half-time at 19, and by 20 I’d ditched my senior year of college in favor of a full-time job. It was entry level and paid sustenance wages, but that still put me a fair sight ahead of my friends pulling $6 an hour from work-study gigs. And by the time they graduated into their entry-level gigs, I’d taken a promotion and changed jobs for a higher salary, and on it went. While those around me job-hopped, went to grad school, explored different fields, or suffered from pot-dot-com-kaboom layoffs, I inched up the career ladder in the same field I’ve been working in since I was 16. So at lunch, I often grabbed the check away from the friend I knew had a harder time than me making ends meet.

And I always did that with my three-years-younger sister, who left college with a fancy diploma and the requisite five-figure debt load that comes with it. I knew she was constantly fighting to keep up with student loan, medical and credit card bills on a salary that was never more than half of what I made. When we went out for dinner or took a weekend trip, I paid.

And then I turned 30.

Suddenly, in the past year or so, a whole bunch of those I hang out with have leapt forward financially. The friend who used to be a broke law-school student got a job at a ritzy white-shoe law firm with an eye-popping starting salary. The friend who was a teacher is now a principal, running her own school. The math grad student became Dr. Bonnie and had two universities bidding for her services. And the friend who completed a social work masters program is head of the human services department in a big city.

And my sister landed her dream job, which pays a very reasonable salary and comes with the unbeatable perk of free housing. (Before anyone gets too envious, said housing is in Ciudad Juárez. It has a lovely backyard — surrounded by alarms and barbed wire.)

Of course, the recession hasn’t totally whooshed by and left my social circle unscathed. I also know people who spent small fortunes on grad degrees and now can’t find work in the field, fellow journalists left stranded as their publications closed, and friends muddling through gigs they’re overqualified for because it’s all they can find.

But instead of being the most financially secure of my friends, I’m now somewhere in the middle of the pack — and falling. Most of those I know are in fields with much better salary-advancement prospects than mine.

That doesn’t bother me in a financial sense (for now — check back in 10 years and see if I’m regretting this whole “write words for a living” thing), but I’ve been surprised by the mental reprogramming it’s required. I still start to reach for checks and then remember — I’m not the only one with regular paychecks anymore. I can let other people leave the extra cash for the tip, or pay a bit more than their share if we all have $20s and no change. Or let my friends treat if they offer, without feeling guilty.

The splitting-the-bill machinations many be a me-specific thing, but I think it’s pretty universal for those in their 30s to suddenly find their whole social-circle financial landscape shaken up. People get married, get promoted out of entry-level gigs, have kids, leave grad school, ditch waiting-tables-and-acting for jobs with health insurance, and generally grow up into situations that are more complicated, but also usually more lucrative. And the salary disparties become starker — instead of everyone being young and basically broke, suddenly some people are doctors or investment bankers making much more than the friends who became teachers and office managers.

The whole thing really hit home for me when my sister came to NYC a few weeks ago for a final pre-Juarez-departure visit. We went to Babbo, where we first journeyed eight years ago in our initial foray into pricey Foodie Nirvana Restaurantland. I saved for two months to field that bill, which came to almost a third of my monthly rent at the time.

This time, after a four-hour wine-and-pasta extravagance, we surveyed the financial damage. I started to reach for my Amex … then realized that for the first time I didn’t have to vehemently insist that my sister put her own credit card away. Thanks to the whole free-housing thing, her take-home pay is probably better than mine these days.

So I left her take care of more than half the bill. It’s an adjustment, but I think I can get used to this.