It's been a long time since I've seen Lorelai. We went through quite an adventure in Business School, both of us being single moms and trying to complete our educations. So, I was absolutely delighted to run into her last weekend in Hartford.

I remember her as vivacious and always on the verge of ADHD: full of life, and plans, and a great love for her kid. A girl, I think is what she had, a grown girl. And she was engaged to a professor, I believe, for a while, but then broke it off for some reason. And what a mouth! I don't think a lot of our profs appreciated her unique brand of 'class participation…'

When I run into her at the little coffee bar we used to frequent, I immediately notice that the years have been kind to her. Much more than to me, I think, patting the twenty-five pounds that kid #2 have left me with. Lorelai looks great; gorgeous skin, incredible body. Who am I kidding? It's more like forty extra pounds. But I wouldn't trade my late-life baby for anything in the world, I think, as my foot tap-taps the stroller and keeps Mr. Monster Kid in motion.

We sit and have coffee, decaf for me, of course, as I'm still nursing. In fact, Mr. Monster Kid's hungry again, so I smile wryly and get him situated.

I can tell by the look on Lorelai's face, the wistful glances she shoots in the direction of my chest, that something's not quite right in that department. I reach out, squeeze her hand, and ask how her kid is doing.

"Rory, oh Rory's great!" she gushes. "Graduated Yale a few years ago, has an on and off boyfriend, and is working in Omaha, Nebraska of all places!"

"Omaha, huh," I murmur.

"Yeah. Small market, gotta start out somewhere, and it's where her boyfriend is."

I notice she's wearing a wedding ring. "So I see you got married after all," I chuckle.

"Yeah, not to any of the guys in class," she laughs back at me.

I quirk an eyebrow at her.

"Come on, don't tell me you didn't date a fellow student or two…"

"My kid was so young then," I explain. "But tell me about your husband…"

"Well, I've been married for a few years now."

"Any kids?" I inquire.

And that's when I see it. The look. The look on the face of a woman who wants a kid, but can't have one. I start to open my mouth to retract my question, but she jumps in.

"No, no, don't feel bad. It's just that, well it's a long story, but let's just say that Luke, that's my husband, had a kid and he didn't want to complicate things at first with a new kid. In fact, we postponed the wedding because of the, I mean, his daughter."

"Oh, that makes sense. Kids don't like it when their parents marry someone else."

"And yeah, by the time the kid got around to accepting things, well, it was too late. Expiration date and all," she adds.

I must have had a perplexed look on my face.

"Eggs. Too old," she clarifies. "Seems time ran out for me."

She looks like she wants to cry. But Lorelai smiles. Despite her sadness, her face fills with joy. "Before I got married, actually, before we got together, I took things...people...for granted," she admits. "But now that I have gone through this, I am grateful for all I do have. Friends, my business partner! Hey, do you remember her? Sookie St. James?"

As a matter of fact, I do, and I tell her so.

"Can you believe she's got two kids, one's almost a teenager!" she tells me, then continues with, "But seriously, I'm grateful for my job, and my husband, and my kid, and of course, his kid. And during a blue moon, for my parents!"

"Oh yeah, I seem to remember you had Mommie Dearest for a mother," I respond. "But isn't it hard," I ask, "dealing with a step-kid? When the 'Yours, Mine and Ours' thing is always in the back of everyone's mind?"

"Yeah," she acknowledges. But she goes on to say that she lives with the fact that she and the love of her life won't have kids, as best she can. There are so many other things she wants, needs, to do. The only regret she has is that she won't have his children. She laughs ironically, telling me about a time when she and her husband, before dating, had discussed kids, and how he didn't really want them. And ironically, his biological clock didn't start ticking really loudly until they were serious.

"So tell me how you two got together," I ask, after we've spent some time talking about my kids, and my husband.

I'm surprised to learn that she'd known her husband for something like seven or eight years before the sparks flew. In fact, Lorelai says she kind of regrets focusing so much on her career during that time, instead of trying to find time for a personal life. "I guess I always thought that there'd be time for that later."

I laugh, remembering how driven and single-minded she was when we were in class together.

But she continues. "It's probably for the best. It would be so much harder to deal with now, Luke's always worried about being an older parent, and possibly leaving a child behind."

Lorelai then looks at me, and Mr. Monster Kid, kind of wistfully. We're so different now. To tell the truth, I am kind of jealous, tied down with children, while Lorelai is off on exciting adventures with her new hotel. It seems she's spawned her own chain of charming little inns.

I finish my coffee, pushing it away with a satisfied smile.

Lorelai does the same, commenting how no coffee is as good as her husband's. She pulls out a business card and invites me to stop by sometime, then continues. "Maybe I'm not missing all that much. Just think," she quips, "I'm always able to sleep in on Saturdays. And whenever I'm needed at one of the inns, I'm able to go at a moment's notice."

I think about what Lorelai has missed out on. Both the good and the bad. I look at Lorelai with her beautiful hair, her exquisite dress, and oh my god, those shoes, and I feel sad for her. She was a super mom to her kid by all accounts--who can argue with having a happy Yale grad in the family? Yet, I also know she was really young when she had her, and that she'd be a great mom now, too.

I think about my own experiences. I mentally compare what it's like to raise a kid alone and then with a committed partner. There's no comparison, I think. I remember how I had to use every ounce of carefully-acquired discipline to keep from running out of the house when the first kid was so needy. I think about how decisive and self-confident I now am, older and more secure and settled.

The look in Lorelai's eyes makes me realize that tears have formed in my eyes.

Lorelai's got to leave, and so do I. I don't quite know what to say. 'See you around,' seems somehow shallow. Lorelai sees my discomfort. "You were a good friend back then," she says, "I'm glad we ran into each other."

She reaches into her beautiful purse. "Say, here…" She scribbles something on a card. "That's Michel's direct email; he's my Manager of Operations. Any time you want to get away, call him and tell him where you'd like to stay. My treat. And we've got great childcare at all our inns…"

"Wow, thanks…" I say.

"Take care," she says as we reluctantly part ways.