This transition you’re going through reminds me of a key moment that occurred within our friendship, many years ago. We were casually friendly at the time, working in the same building, but nowhere near as close as we are today. Your tales of the single life were entertaining as hell even then, especially to an unhappily married man. The stories of your single girlfriends and their misadventures in the land of love were better than late night cable. Even then I knew you were a good girl who was always good, even when you were being bad.

I’m talking about the time you signed up for a singles vacation. I forget the exact name of this excursion to debauchery, but I remember two of the words in the title were, “Hedonism” and “Jamaica.” At the time I said, “I’ll bet you all the money in my pocket (and I was rolling in it those days) that this will be the last time you’ll go near anything remotely resembling a singles vacation, for the rest of your life.” You came back from the trip a changed woman. You realized you’d outgrown that scene and had begun the process of outgrowing that life. It seems to me that you are simply taking the final step in this process these next few weeks. It’s been a long journey for you, as evidenced by the tear and puke stains on TNG’s favorite new piece of furniture.

Being a quality wingman (or wingwoman, in your case) is wildly overrated. If we’re not getting laid, it only serves to reinforce our feelings of being a loser. If we’re in a relationship, it makes us long for the single life. Where exactly is the joy in riding another’s wing? On the other hand, riding the wing is somewhat akin to phone sex… we get to enjoy the ride, without the pressure and responsibility of piloting the plane.

There’s a twisted nobility to covering for a married friend. Chances are you were the only one they could trust with a secret so deep and important. Chances are you were the only one with whom they could be certain they would not be judged. Chances are you were only ten minutes away in afternoon traffic. This may say bad things about them, but it says only good about the kind of friend you’ve always been. I have no match for your rumpled sheets, but I’ve certainly logged enough hours covering a married ass or three in my life. I never felt guilty about it. I never felt morally responsible. To me, true friendship trumps just about anything. I never felt like an accomplice, I only felt like a friend… a damn, good friend.

The trick isn’t worrying about your married friends and the world you’re leaving behind… the trick is making sure the flip side of that never becomes your world to begin with.

When I was a little kid, there was a commercial for a cereal that was supposed to be good for you. None of the kids would eat it until the older brother told the younger brother, “Try it, you’ll like it.” That cereal is still on the market after all these years. However, Mikey, the child actor from the commercial who tried and liked the cereal hasn’t been heard from since… I don’t think it took eighty stitches for him to find another line of work.

Does it really matter if a man and a woman have shared activities? Every time I read about a couple who loves to do the same things, they’re either gay or AARP members. I once had a girlfriend who was as committed to exercise as I was. It was only a matter of time before we tried exercising together. First we went for a run. I’m 6-3, she was 5-3. My legs reached up to her all too perky breasts. By her mile two, I was on my mile four, and she was pissed off that she hadn’t brought her iPod. Failing at that, we tried her favorite exercise, the female favorite – spinning. I hated the idea of spinning, but I loved the idea of her and me naked after a sweat and a shower, so I joined her. Midway through the class, I fell off the bike, jamming the leg of the rider next to me into her pedal and drawing blood. I haven’t been to a spin class since. My life is pretty simple. I play basketball, lift weights, play air guitar, drink beer and hang with my kids. Do I want or need someone to join me on any of these endeavors?

Shared activity is relationship cotton candy in my book, but shared interests on a minor scale can often be relationship gold. I may not need to share my hobbies and passions with a woman, but if anyone is keeping score I confess to assign major importance to the following factors in a relationship for it to have any chance of lasting beyond “I had a nice time tonight.” And here they are:

Food: The MOST underrated component of any relationship. Overweight she simply cannot be, but if a woman doesn’t love food as much as she loves sex (and both have to be A LOT), we simply have no chance. Drink: I’m no alcoholic, but I once tried dating a recovered alcoholic and I gave up early. I’m hardly in need of a woman that will pound shots of tequila and throw up on my loafers, but if she can’t enjoy a nice glass of wine with dinner or a sip of champagne at a party, then we probably won’t be generating much in the way of positive momentum.  Television: We all watch it… we all have our favorite shows… we all use it to enter the check-out zone. One of my oldest friends has mentioned a thousand times how much he wishes his wife would sit next to him and watch PGA golf on TV every once in a while. I never know how to tell him how lame that is. In my book, as long as she doesn’t ask me to watch Bravo and she doesn’t mind me watching ESPN, we should be good to go.

Keep it simple. If you’ve learned how to stand in the batting cage and drink from a beer bong, you have more street cred than any woman needs. You gave it a shot and it wasn’t up your alley. Hang up your hiking boots and break out the black teddy (after your stitches come out). I doubt TNG will mind the tradeoff.

You’re a smart girl. Smart girls know when it’s time to be one of the boys… and when it’s time to just be a girl.

Of course you’ll make it. You’ve already made it. The only question remaining is what exactly is this “it” you’re trying to make?

Don’t ask me. My life is more defined by my divorce than it ever was by my marriage. My marriage was a sham, mostly because I had no idea who I was and I chose to marry a woman who was right “on paper,” but nothing close to right for me. I have an excuse – I was very young. We both were. There ought to be a law forbidding people to get married before the age of 30. It might drain the world of some romance, but it sure would lower the divorce rate. (UN) fortunately for you, you don’t have youth available as a go-to excuse. You’ll have to find a much more mature excuse if need be.

Don’t ask your Mom. What does she know? She cheated, the guy she cheated with was cheating, their respective spouses were cheating… and all this before you were born. Fast forward to now and she’s all alone, not by choice. She still has her children, but after lying to them for a lifetime or two, their pipeline of unconditional love operates at more of a trickle than a flow. I think it’s safe to say that as far as your marital approach will go, you’ll be one apple that falls not just far from the tree, but miles from the orchard.

Don’t ask John. He’s a friend of mine who admittedly “hates” his wife. He’s only staying for the kids. Lucky kids. They get a miserable set of parents to emulate as they mature and begin to formulate their own romantic relationships. At least John’s having an affair too. He tells me she’s a nice lady with whom he has much in common, besides grabbing a quickie while running errands on a Saturday afternoon. Her husband left her for a younger woman and she’s foreclosing on her house because he won’t pay alimony.

So who exactly can you ask? You can ask my sister. She has one of the best marriages I’ve ever seen. They love each other AND respect each other. After 25 years and three kids, they still make time for just each other. They may certainly need each other, but a blind man can see when they’re together that they also still want each other.

You can ask a female ex co-worker of mine. She’s known since the womb that when she got older she would find the right husband, raise a family as a stay-at-home mom, spend all her time together as a family and live happily ever after. It’s only been 12 years, but so far she is living that exact life, and loving it as much as she always dreamed she would.

You can ask a million people their thoughts and dreams and ideas about the step you’re about to take and you’ll get a million different answers. The only voice that matters is yours. The only life you’re living is your own.

So, stop listening to other people (except for me)… especially other women. Either they mean well, but push every scared and insecure button inside of you or they don’t mean well and they do the exact same thing, except it’s on purpose. And stop thinking about how you look. He knows precisely how you look. He knows every pockmark, every extra hair and every extra five pounds you think you’ve been hiding so well. And where is he? Oh yeah, right there, still next to you, waiting for you to make his house a home. And stop thinking you’re the only one of the two with strange kitchen and nocturnal habits. He’s a dude. I guarantee his laundry list of oddities will do yours complete justice.

Most important, don’t stop having sex… don’t EVER stop having sex.

I think your friends have been watching too much E! News. Unless you changed your last name to Kardashian and TNG wears an NBA uniform for a living, save the $400/hour you’d pay some lawyer for sucking the heart out of your marriage before it even begins… You can put that money towards hardwood floors instead.

The concept of a prenuptial agreement tickles me deep within the most cynical bones in my body. Do you know what I would like? I would like to have an absolutely filthy rich woman fall hopelessly in love with me. I would like to feel equally as deeply in love, and grateful, the way women often do when they get so “lucky.” I would like to talk marriage and future and growing old with a shit-eating grin on my face because I am so damn happy to be having this conversation with the woman I love, who also just happens to be filthy rich. And as we stand hand-in-hand, at the entrance to marital heaven, I would like to sign a prenuptial agreement… protecting her, not me. If I had to sign a hundred documents to insure that my future spouse’s assets revert back to her should we fall apart, I would sign a hundred documents. To me, it’s a no-brainer. Sometimes I wonder why most women I hear about under these circumstances don’t feel the same way. If you love someone enough to marry him or her, what does it matter if you have to sign an agreement to prove it?

On the other hand, why would anyone fall in love with a man or woman who would insist on a prenup in the first place?

You know what a colossal financial beating I took in my divorce. She got more than everything, I got less than nothing. I could have done it differently. I could have played hardball. I could have hired lawyers and drawn up contracts and put together spreadsheets designed to squeeze every penny from her pores. I could have “punished” her for our lousy marriage by forcing her and the kids to change their address, their friends, and their lives. I had no interest in doing that. I gave her everything. Our “stuff” meant nothing to me… not the house, not the private schools, not the suburban dream we’d been pretending to share for so many years. I didn’t care about anything that might have been outlined in a prenup and I certainly didn’t care about myself. I only cared about the kids. What would a prenup have said about them? How would a prenup have addressed anything as important as them?

So your friend thinks you should have some sort of guarantee? Says who? Some couples get divorced after thirty years, some couples get divorced after thirty minutes and some couple actually do live happily (well, relatively speaking) ever after. Since when does any relationship, including and especially a marriage come with any guarantees? I hate to break it to every little girl reading a fairy tale in bed tonight, but there simply are no guarantees in life… or marriage.

Now about that wedding…

I hate weddings… and I love weddings. I hate weddings because of the Grand Canyon sized gap that is created between what they represent and the actual marriage that too often follows. I love weddings because of the true love they aspire to represent and the joyous union they earnestly guarantee will follow.

On the surface, what’s not to like about weddings? Shrimp the size of tennis balls, and enough of them to feed Texas… Glorious amounts of free alcohol from the top shelf and wine and champagne flowing… Women looking as beautiful as they can possibly look, in dresses from the pages of Vogue, makeup as if done for a late night talk show, enough prep time to get themselves just right and a twinkle in their eye that makes a man want to fall in love and get a room, preferably in the next ten minutes… Middle-aged people dancing for the first time in a couple of decades and the funny relative you haven’t seen since the last wedding you attended. Most of all, a man and a woman with the courage (some would call it lunacy) to think that they will be one of those special couples that will grow old together and be happier forty years into their marriage than they are today.

Of course, there’s the flip side of weddings as well. I went a wedding last year that must’ve cost more than my first condo. That couple is already separated and sprinting toward divorce, if not outright annulment. A girlfriend once told me a story about the limo ride to her wedding when her father told her it still wasn’t too late to call the whole thing off, despite the church, the reception, the booze, the cake and all the pomp and circumstance poised to explode. Five kids and twenty years later, she’s renting a house and scrambling to make ends meet while he plays online poker for a living and refuses to pay child support. Not to mention the time when my friend, THE GROOM was caught with his pants down and one of the bridesmaids on her knees in front of him, giving his popsicle all the attention she could muster. He later told me that the thought of only having sex with one woman for the rest of his life had suddenly made him sweat through his tux and he needed one last episode to calm his nerves before the wedding. Ironically enough, they’re still together. I’m not sure what ever became of the bridesmaid.

Even a cynic like me believes that every girl is entitled to some version of her dream wedding. It doesn’t seem fair to drill the princess wedding fantasy into every little girl growing up, only to chastise them for holding onto that fantasy into their adult years. You’re as entitled to your fantasy as any little girl should be.

Just please don’t do Vegas… Nobody should EVER get married in Vegas.