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Yep, as I explain to Izzy, I’m going to be in Manhattan next month, escorting Billy Fox on the press junket for the premiere of his latest movie. And wouldn’t you know it, “The
Boss” added another NYC night to his concert tour that falls smack down when I’m in town. Simon and I are both lifelong Bruce Springsteen fans. Izzy—who still mourns the closing of legendary punk and New Wave venue CBGB—not so much. But she totally doesn’t care that Simon and I will go together without her.

As a senior editor at
Vintage
, Izzy occasionally interviews celebs, but only when they really know their wine or buy a vineyard or something. And then
Vintage
runs a one-page Q & A about the star’s favorite wines or obscure spa getaway. I suppose it could seem like a conflict of interest. And I’m not going to lie, Izzy and I definitely mix business with our personal lives. But she can get celebs without me, so when we help each other out, we’re not crossing any boundaries. And, let’s face it, there are much worse examples of nepotism in Hollywood. At least we’re both good at our jobs.

You wouldn’t believe the number of assistants and junior publicists I have to deal with every year here who are the kids of celebs or investors or whoever. They march around with their
venti
Starbucks and size 0 Seven jeans and act so entitled. This one recent grad, Denise, is a perfect example. I don’t think I saw her answer the phone once the whole time she “worked” at
Bennett/Peters. It got so bad that Elle finally had to put her well-heeled foot down and remind the assistants pool to stop flipping through
Glamour
and
Vogue
and actually
assist
the publicists. Denise left less than two weeks later for medical “exhaustion” reasons, surely disillusioned that her life wasn’t turning into a
The Hills
–like fantasy.

Charlie is their two-year-old son. He is the cutest kid ever. Like ready for his own Gap Kids ad adorable. Yes, sometimes Izzy’s luck makes me a little jealous—envious, I mean. It’s just that when Izzy and I were in eighth grade, we shared a plan as to how our lives would unfold. We’d each meet a great guy, get married in front of all our friends and family, and then give birth to a boy first, followed by a girl. We were going to live next door to each other and our kids were going to be best friends. It seems a little naïve now, but to a couple of close twelve-year-olds, it was our blueprint to happiness.

My competitive side uncomfortably rears its ugly head occasionally to remind me that I am the one who is behind. I mean, I’m totally happy with my life, and with Jacob. He
is
that
“great guy” I envisioned years ago over tall glasses of Sunny Delight. But it’s been two years, and he has never brought up the M word. It’s beginning to feel like a problem—as if this is it, prepare to settle or move on. Yes, I’m guilty too of falling into an easy rut, and I am still girly enough to want Jacob to make the next move. Or maybe I’m just lazy.

Or scared.

Izzy, per usual, is an apparent mind reader.

Ahh, I wish Izzy would let this go. Like six months ago, Jacob planned this awesome weekend for us. We flew up to San Francisco, saw Dave Matthews Band in concert, and did all the San Francisco touristy things, like riding the trolleys and visiting the sea lions off Fisherman’s Wharf. Even though I’m a California girl, I’d never truly explored the Bay Area. It was a really fun weekend, packed with postcard views and insanely delicious meals. Except that both nights, I got all dressed up
thinking that this whole trip was a big buildup to a proposal. I even secretly called Izzy from the hotel bathroom, telling her how he was behaving and all the romantic plans he’d made. We whispered and giggled over what the ring would look like and what he would say. I had a $100 bet that he would go down on one knee. That’s the kind of guy Jacob is—very traditional.

Except that he didn’t propose.

And after all the effort he put into the trip, I couldn’t exactly behave like I was upset about it. It took me two days to call Izzy back because I was so embarrassed. I knew I didn’t have to tell her—I mean, if he
had
proposed, I would have called her the second I could to give her the good news. She knew he hadn’t and I just didn’t have the courage to talk about it.

Even when instant messaging, Izzy is a very perceptive person. Sometimes it’s frustrating because I can never get anything past her, but the opposite is true too. She knows when to back off and give me my space. I’m the first to admit that I don’t
have the best track record with men. When the going gets tough, I’m usually the first to pull the parachute. But only because I don’t want to listen to some pathetic excuse the guy will come up with to break up with me.

Being with Jacob is the first time I don’t feel in control. And it’s a little unsettling to feel the old—if dysfunctional—dynamic shift. Izzy assures me it’s a sign of maturity; that a little vulnerability and trust in the unknown is a positive thing in a relationship. I’m cautiously optimistic but still need (or want) to know where the parachute is hidden.

Weekends are never long enough. Saturday morning
is often dedicated to sleeping in or nursing the hangover I’ve earned on more sociable Friday nights, so forget working out or attempting anything productive until after noon. Then the rest of the day is spent catching up on stuff I can’t get done during the week, like errands and paying bills, and Sunday is practically ruined from the beginning because
tomorrow
I have to go back to work. I remember this particular TV show that aired when I was beginning high school. It was about a girl who could stop time by clapping her hands together. Now,
that
is a superpower I could get into. I would go nuts with a gift like that, freezing time to think up a clever retort or witty joke. But mostly I’d freeze time so I could sleep in as long as I wanted.

Tonight Jacob and I are meeting his best friends, Damon and Travis, for sushi at Katsuya. I had the fortitude to make the reservation for a party of six because last time we all got together at a trendy restaurant, we waited an extra half hour while the annoyed hostess found us a bigger table for Damon’s last-minute arm candy, an unbelievably bitchy former Playmate. I was starving by the time we got seated, and
perhaps
a little affected by the apple martinis I’d consumed on an empty
stomach while waiting at the bar, and therefore a tad bitchy and more forthright than usual myself. So you can just imagine how the evening escalated. Jacob almost choked on his bacon-wrapped date when I asked Ms. Playmate how difficult it was to move past her career working “the pole.” How was I supposed to know it was true?! She screamed at Damon for telling us how they met and stormed out. Needless to say, that’s why we’re at a new venue tonight. I doubt they would even let us in the door again at the other spot after that scene.

Damon may be Jacob’s buddy since far back in high school, but it’s no secret that he gets under my skin. We didn’t get off to a good start. I’ll never forget hearing the way he mercilessly teased Jacob for not still playing the field after we first met—preciously calling me “the Little Woman” and always undermining the emerging relationship. I swear, it was like he was threatened or something. With Jacob as our mutual bond, we’re forced to share tables and play nice. But neither of us is exactly volunteering to chair the other’s fan club.

In sharp contrast, as much as I loathe Damon, I adore Travis. He reminds me of the carefree frat boys I used to hang out with in college. He’s still living the frat life; only now, he owns his “frat house” and prefers imported or craft beer over a keg of Milwaukee’s Best. Jacob and Travis met as associates at the same investment banking firm. It’s funny to me that Jacob and Travis instantly bonded—in that weird way that guys “bond”—because from Travis’s now-long surfer-boy sandy hair to his Harley-Davidson motorcycle, he is seemingly Jacob’s polar opposite.