How to romance a divorced bipolar almost-40 MILF with two kids under the age of 10

1) Check cojones, male or female. Are you strong enough for this? Dating a dee-vor-SAY is never simple. Wooing a single mom is no project for the weak. Smother the whole mess in Sylvia Plath chocolate depression and Van Gogh caramel de bipolar, and you’ve got a mountain to climb, pal. Blindfolded. Backwards. With black dogs nipping at your heels and those flying monkeys from the Wizard of Oz batting at your head.

2) Sure you want to do this? Hot partners with less baggage ARE available. No, seriously. They are. Join clubs, do a little matchy-matchy on Match.com, skydive. Still think you’re up for a divorced bipolar almost-40 MILF with two kids under the age of 10?

Damn. You’re a superfreak! Superfreak! You’re superfreaky, YOWWWW!

Continue to #3.

3) If she says she loves and respects her ex, believe her. But if this bothers you, walk away. Your wooing will not make her unlove anyone. Some people do not unlove. This can be a nice perk, because it means she won’t unlove you, either, someday, if things go to hell in a medicine bottle.

The lovers who don’t unlove? They weep. A lot. Are you prepared to hold her while she weeps about the loss of a great love in her life? Or would you rather she lied to you? Didn’t say anything? If you’d rather she kept her mouth shut about her losses, best skip town, try again elsewhere.

4) If she says she hates her ex, and she’s over him completely, tread cautiously. This may indeed be true. But ‘hate’ is a strong word. And if she hates him, it means she has it in her to hate you too. Don’t rejoice, don’t be smug. ‘Hate’ can hide a whole bunch of nasty, conflicted, miserable feelings, like a tarp over a beat-to-hell Chevy in the front yard.

5) When she says she’d give her life for her kids, believe her. She’d give her life for her nieces, her nephews, her friends’ kids, even strangers’ children. On the day she became a mother, she became a mother to the world.

If you have kids, even though it makes life more complicated, she’s relieved that you understand. If you don’t have kids, she wants to know why. She’s watching you.

If she lets you meet her kids, that’s a big deal, buddy. Be yourself. Listen to them. Remember they are people first, kids second. They are individuals, and as much as they drive her crazy (crazier?), they are everything to her. They come first, and always will.

If this is not what you want—kids and all that comes with them—it’s all right to say so kindly, and move on. She will understand. Parenthood and step-parenthood are not for the faint of heart. You may very well be better off in a kid-free life. That’s okay. That’s okay for all involved. More than okay.

6) Bipolar disorder is a real bitch. She’s not a bitch, but the disorder is. If she’s non-compliant—skipping doctors’ appointments, not taking meds, drinking heavily, doing recreational drugs, staying up all night, cutting, not eating or showering—she needs help and isn’t in a place to be a partner. It can be that she’s tried everything, and feels hopeless. Again, she needs help, not a boyfriend or girlfriend. Can you point her in the right direction again, as a friend? It can be rough stuff.

If she’s doing all she can to manage the illness, this is one tough chick. How tough are you? She’s going to have quite a lot of down-and-out days, despite appearances. Her brain whirls at the speed of the train that she can’t recall the name of. Her heart plunges into the depths of tar-pit despair in an instant. She is frequently certain that she’s a loser beyond salvation, except when it comes to her kids. Chances are good she’s giving that aspect of her life her all.

The peculiar fact is, a bipolar parent—when the disease is under control—can be a heckuva lot of fun. Their offspring frequently blossom, because the parent in question radiates life and creativity on good days, and a willingness to talk about the hard, sad stuff on the bad days. The bipolar MILF leaves room for everyone around her to be an odd duck. This is kind of a groovy thing, if you’re hankering to let your inner odd duck out in a safe place.

Freak flags fly around the bipolar bears. If freakiness outside of the bedroom makes you uncomfy, move on. If your life plan includes embracing your inner freakshow, then you may just be with the right woman.

7) Let’s address this MILF thing. We’re assuming you wouldn’t be sniffing around if you didn’t find her attractive. Let her know. While they keep a bear off the window ledge (most of the time), bipolar drugs do dreadful things to the bod and the brain. Shaky hands, wide-load rump, lurching gait—none of these things makes her feel too sexy. If you find her beautiful, tell her. It won’t get old.

However, she’s bipolar AND she’s pretty sure she’s getting old. Veins. Cellulite. Wrinkles. Gray hair. The stress of the bipolar disorder speeds up the aging process, and if you haven’t noticed, she has. And she’s horrified. Again: tell her she’s lovely. Better yet, as bipolar and the drugs to treat it turn her brain into Swiss cheese, write it down. Write her love letters. Draw her pictures. Compose a poem or two. Plan a special trip, with patience (planning around children and custody and dogs is one big tangle). She will love a chance to escape her complicated life.

She thinks the concept of a ‘MILF’ is hilarious, and a tad worrisome. Is the ‘F’ part all you’re after? If so, do please move on. Girlfriend’s been through a hell of a lot. But if she’s also a MILH (hold) and a MILL (love), do stick around. You’re special.

If you do want to sleep with her someday, don’t tell her a million times how horrible it would be if she ever got pregnant again. Bad move, Jedi. She’s a smart lassie and knows the last thing she needs is another kid. But she likes to think it wouldn’t be the Apocalypse, either.

If you don’t want to sleep with her because she’s not able to make a commitment, and frankly, girlfriend freaks you out some, okay. But find other ways to let her know you haven’t written off the ‘F’ part of ‘MILF.’ Or she’ll assume there’s even more wrong with her than she thought there was yesterday.

9) If you’re frustrated by her slowness on the commitment front, think about it from her perspective: the single thing she thought she’d gotten right in life blew up. The one stupid thing she thought she got right. Now she’s mired knee-deep in smithereens of her past, completely humiliated. Don’t try to argue it away. It just is.

And now, she determined to take her good old time, this time around. The failure of her marriage is the greatest devastation of her life so far, and she’s not anxious to repeat that.

She doesn’t want to let anyone down. She doesn’t want to let herself down. She’s not convinced that marriage is such a groovy move, not anymore. She’s not even sure that anything but casual, 1950s soda-counter dates are a bright idea. That’s a pretty big wall to come up against, and it’s not your fault, not one bit. Don’t take it personally. Take what you can, and when you can’t take anymore, say so. Kindly, please. Bipolar bears devastate easily. It’s not melodrama—we are talking genuine, killer feelings of serious, slashed-to-the-core wretchedness. But bipolar bears, like anyone, prefer the truth, in the end.

10) How does your family feel about her? Oh, now, that doesn’t matter, you say. It only matters what I feel about her. [Cue game show buzzer]

If she knows your family dislikes either her or her situation, then you’ve got a situation, whether you like it or not. She’s a mama bear, and that mama bear won’t be eager to lead her cubs into hostile (or even merely tense) territory, not at least until she is sure beyond a shadow of a doubt about you. She may even love you, and still not be sure. With young cubs, the stakes are through the roof for just about every move she can make.

So be willing to work out your family crap. Be willing to work hard to create the kindest environment you can, on your home front. That will not go unnoticed, or unappreciated.

11) How much leaning can you stand? How big are your shoulders? In a perfect world, a relationship would be 50-50. In this world, a regular, run-of-the-mill relationship hops from 30-70 to 60-40 to 20-80, as necessary. In Bipolarville, well, girlfriend’s gonna need a hand. Maybe more than the usual galpal. Bristling at that? Insisting on fairness in your head? Steer clear. It’s fine. You know what you want, and that’s more than most folks.

Bipolar mama bears on their own are navigating the single mama terrain, but with more difficulty. Doesn’t mean they’re wimps. On the contrary. If they’re upright and smell nice and their kids are passably happy and smell nice too, then they’re Herculean. But the air conditioners probably haven’t made it into summer windows. The back porch is probably a humiliating junk yard. The dogs’ barking is possibly triggering anxiety attacks. The shampoo may be singing rock operas. Preparing meals is often beyond a bipolar mama’s coping limits.

Do not embarrass her by curling your lip at the cereal bowls at dinner. Do not say, “You needed a nap AGAIN?” Her meds are the equivalent of the tranquilizers used at zoos, when the rhinos get loose. Don’t believe me? Read up on it. The bipolar mind is Speed Racer on crystal meth, without the fun (unless you’re a lucky manic type who whizzes through life without much misery, just maxing out credit cards and sexing it up with random strangers). Patio umbrellas terrify her. She frequently bawls her eyes out on the floor of the tub, without knowing why.

If you like a life without chaos, if you like your women completely independent and predictable, then you are howling up the wrong tree, trust me. She doesn’t want to tell you, but she needs some help. Okay, quite a bit of help. She often feels like she is drowning, and she has no idea to whom to turn, even though she knows things like when to use the word ‘whom.’ She is pretty damn sure she’s exhausted everyone in her life, and the last thing she wants to do is exhaust you. So she won’t say much. But it will register if you seem to be keeping tally of what she needs, what chores you’ve helped her with, how many times you’ve made dinner. Not in a good way, either.

12) She can give you the stars, the moon, eyes that see into you, hilarious observations, enormous affection, a fondness for adventure, and more passion than you can imagine. She is game to pitch in when you need help. But sometimes, she’ll be incapacitated. Sometimes, she won’t be able to work. And you’ll have to step up to the plate without resentment. That’s the hard truth. And there will always be her family, and her ex, and her kids that will expect you to be a bridge to her when she goes into hiding again.

Again: Are you sure you want this, when you could have something—and someone—else? Think about it. In the words of Billy Joel (because bipolar bears are prone to quoting Billy Joel lyrics, something you won’t find in the medical journals): she’s a real nice girl and she’s always there for you / but a nice girl wouldn’t tell you what you should do.

So I’m telling you. Consider yourself enlightened.