Miss Information

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Dear Miss Information,

I'm a (mostly) straight female in my late twenties, living in Brooklyn. My boyfriend of three years is in his mid-thirties and lives in the Bronx. We have a great relationship, we're both GGG, and we communicate really well. We're crazy in love. The sex is amazing. We're planning on moving in together soon, and we want to eventually start a family and all that jazz. The problem is he's broke. Like about $150 grand in debt broke. And almost $100 grand of that is in student loans. He's got a master's degree, but doesn't make enough money to even begin his payments. He's sort of told me all this before but I guess I didn't realize how real it all was until last night. He was explaining his money stress to me and I started crying because I just saw the future I want falling away. If I choose to be with him, I'm afraid I'll be choosing a life with ongoing economic problems.

I went to a very expensive undergrad college, but have worked hard to make my payments on time every month since graduation and have been slowly chipping away at my debt. I have no credit-card debt at all and an almost perfect credit score. I have a good job, but not enough income to support a family by myself — or enough income to help offset my partner's debt. I know this is so selfish of me and I'm so embarrassed for feeling this way, but I've worked very hard to be financially responsible, and now it feels like that's all going to go to shit if I start to build my life with him. I want to be with him, but I also want financial security and a kid and a house and a picket fence. Okay, maybe not a picket fence, but you get the idea.

Am I Being Awful?

Dear Am I Being Awful?,

Your letter takes me to the edge of an abyss called "legal advice," which — disclosure! — I am in no position to dispense. (Let me put this another way: do you want legal advice from a woman in sweatpants?) Luckily, our commenters are a strikingly book-learned bunch, so guys, feel free to jump in with any helpful lawyering. (That's better — take financial/legal advice from internet strangers! Who, okay, fine, are also wearing sweatpants.)

You're doing the right thing by taking a hard look at logistics before you jump into marriage. Luckily, you've got some time to change things before you put a ring on it. Go ahead and move in together, but keep your finances separate. Once you do get around to marriage, a pre-nup is a sound option: sure, the word conjures a bleary-eyed Anna Nicole Smith, but pre-nuptual agreements are no longer the sole realm of the gold-digger. A pre-nup allows you to separate your finances — including debt — from your fiance's. (I am told that debt doesn't automatically transfer in case of marriage, but each state has maddeningly different marriage and divorce laws.)  It's also a good idea to keep separate checking and savings accounts, and to file taxes separately.

I know, none of this makes for sexy conversation — and, actually, much of it is pretty delicate to talk about. "Baby, I want to have your children, but I'll claw out your eyes if you touch my credit score." Ego and money are almost inextricably tied, and when institutions like "family" and "children" get concerned, existing tensions get heightened. The more you can practice discussing dicey issues in a loving tone before you get married, the better. Look at this like a practice run.

To that end, it may be worth sitting down with your boyfriend and helping him figure out a plan to stabilize his debt. Set a timeline: if you want to get married in two years, try to have his debt reduced by x amount within one year. It may very well be that he's gotten paralyzed by the avalanche effect of his debt, and simply having a plan to dig out of it — especially assisted by someone as financially responsible as you — might help. But, of course, remember that it is his debt, not your debt: appreciate that this is likely sensitive and nerve-wracking for him, and try your best to guide without trampling. 

By the way, "holy God, how are we going to afford a baby?" is a question almost every couple ever asks themselves, crippling debt or no. Start small, and work on what actually impacts your life — the apartment, the stellar sex, paying down loans — before you start heaping on children and picket fences. The price of cribs will always be terrifying; trust that that will stay unchanged. Work on the "today" things, and don't worry about the big questions until they become relevant.

Dear Miss Info,

I'm turning thirty-five this year, and as these things go, I'm getting introspective. I've never been in a romantic relationship. I've had sex, but it was emotionally one-sided. (My side, to play against stereotypes — I'm a guy.) I lost my virginity at twenty-eight and have only been with two women sexually. I moved around a lot in middle and high school, so I never dated or had sex or really got a chance to build a identity outside of "The New Guy."

I had money problems in college, so it took me much longer than most people to finally graduate. At thirty, I went to graduate school, and of course most of my peers were twenty-four or twenty-five. This is a long-winded bit of background for my problem: I'm most often attracted to younger women, usually women eight to ten years my junior. This isn't inherently a problem, except for the fact that I often fear I'm in a state of arrested development.

Compounding this issue is my attitude about twenty-somethings. I find that I'm happier among my age peers in most situations. There's just a common language among the people who grew up in the same decade that's hard to get with someone who's younger or older. But as you've acknowledged in your column, twentysomethings are often in a place of finding themselves emotionally and sexually, and I feel like I'm in that same place, at least as it relates to romance and sex. I relate to my own age group in almost every way, but relationship-wise, I relate to people ten years younger.

I've been on a blind date or two with women my own age, and the chemistry hasn't been there. But when I've hung out casually with my roommates' friends or my grad-school chums (all twenty-somethings), I've been attracted to them and have even been flirted with (which never goes anywhere, but hey, I'll take it). Is there a good way to approach this problem as is? Am I misreading my own situation and worrying about nothing? Should I include a joke about a grim-faced man and a gas-powered cow-puncher?

No Country For This Old Man

Dear No Country For This Old Man,

Admittedly, I did not read or see No Country For Old Men, so your references are lost on me. But what a reference "gas-powered cow-puncher" is! Consider it Netflixed. What stands out most in your letter is a tremendous amount of introspection. Your overall tone sounds evenhanded and logical. Cow-punch away!

One nitpicking point, though. You say you've been on blind dates with women your age, and that you hung out with nubile young friends-of-friends, right? And you're distressed that you found the younger girls more attractive? This seems less like a problem of age than a problem of context. "Blind date" is almost always going to be more awkward than "hanging out." The younger women chilling with friends have the benefit of being in their element, while the older women on the dates were probably wearing uncomfortable underwear and sweating over the decision of lobster vs. ravioli. Put another way: in which setting do you think you came off as cuter and wittier?

You notice you are habitually attracted to these young women, but you also recognize that you have deeper relationships with people your own age. With an internal compass like that, you can't go too far astray. Ageism only gets into "danger" territory when coupled with denial. ("Doing ecstasy with her college friends keeps me young!") Your finger seems firmly on your own pulse, which is great.

Struggling with romance and sexuality isn't exclusive to one's twenties, so you're not necessarily behind the curve. Now, instead of fretting about what you're doing wrong, keep an open mind and see what happens. You may find twenty-five-year-olds so mature they blow your mind. You may find thirty-seven-year-olds who act closer to twenty. Let go of the specter of wrinkly, robed Hugh Hefner, and flirt with anyone who seems interesting. You may be surprised where sparks fly.