My problem involves family and money, which makes it sticky as hell. And if only it were family wanting money from me. That I’d know how to handle.

My dad is 60. All my life (36 years) he’s run a family manufacturing business that was started by my grandfather and employs my uncle. It was always my dad’s retirement plan to sell the business when the time came and live off the proceeds. And in the past, that was actually a viable option. However, times are what they are, and manufacturing is in the toilet — my dad’s business along with it. Now it looks like the business will fold and that my dad will need to get a job. Or that’s the version I, the daughter who lives 2,000 miles away, hears from him. My brother hears much more — including the fact that the business is actually going into bankruptcy, and that it was never correctly incorporated (Dad isn’t really great about details or about paying people — like lawyers — even small amounts of money for things he thinks he can do himself). This means that his creditors can go after his personal assets as well, such as his house (which he built). It’s all awful, and it was largely preventable if he’d only done XYZ and put his stubbornness aside long enough to follow some advice.

The thing is, my husband and I are doing pretty well. Really well, actually. My husband worked for a software startup at the right time, which got bought at the right time by the right company and wasn’t too hurt by the bubble popping, et cetera et cetera. It’s not a sick amount of money, but it is money. And, though we both definitely consider it “our” money, the fact remains that I did nothing to cause it to happen — my career path tops out in the mid-five-figures, period. The truth of the matter is, we could write a check for my dad’s business debts today and not miss the money — at least for a while.

I read this, and think, “What’s the problem?! Just do it!” But in reality it’s all weird and uncomfortable. My husband wants to help, but is weirded out by the thought of loaning (oh, who are we kidding, GIVING) my dad this much cash. I’m weirded out both by asking my husband to do it (as it’s not really my money) and by asking my dad to take it. And my dad has always been weirded out by The Money every since it came, and very well might not take it if we offered. The closest I’ve come to talking to him about it is to say, “If there’s ever anything we can do…” which sounds incredibly lame and vague, and to which he always responds, “Oh, I’m fine, everything’s going to work out.”

On one hand, my dad is a grown-up and a lot of his problems are his own doing and responsibility. On the other, my dad was always there for me financially and otherwise when I had some serious problems in my early twenties. I want to help him. He’d do it for me. Obviously, I can’t stand by and watch him lose his house just because it would be weird to give him money…ARGH! It makes my stomach hurt! And I can hear everyone going, “[snort] I should have such a problem!” We have people to help us figure out the legal and fiscal side of helping — I need help on the human side. What do I do? How do I do it?!

A Good Daughter

I’m writing to you because I think I need someone older and wiser to
talk some sense into me.

I’m a sophomore in college, and for the past three years I’ve been in
an on-and-off relationship with a friend of mine. This past summer, we
wound up getting back together, in the sense that we have revived our
romantic relationship but both vow to “keep looking” for someone new at
our respective schools — someone who may not be as good but has greater
propinquity.

We get along swimmingly, never tire of each other, are completely open
and honest with each other, and have amazing chemistry. He is the
gentlest guy I’ve ever met, has never been abusive in any way, and his
top priority is to do everything he can to prevent hurting me. In
short, we adore each other, and when we’re together things are pretty
much perfect. He has one flaw: the idea of commitment terrifies him.
This bothered me before I went to college, but now that I’m here I know
that being tied to someone far away just isn’t what I want right now,
and I like having silly crushes that come to naught and knowing that I
could meet someone at any moment. I also like having him to fall back
on, to use as a sort of “secure base” from which I can wander and
explore, knowing that I’ll never really be alone. He feels the same way.

The problem is that I’m terrified of letting go of him, even though I
think that it may be for the best (at least for now). As completely
clichéd and stupid-teenager-ish as it sounds, I’m afraid I’ll never
meet anyone else with whom I can feel this comfortable and happy. The
number of guys I’ve been really attracted to in my life — where “really
attracted to” is defined as “able to think about kissing without
becoming nauseated” — can be counted on one hand. I’ve gone on a few
dates with other guys, but nothing ever even began to fall into place
the way it did with him (the last date I went on, which was with a very
good friend of mine, the guy put his arm around me while we watched a
movie and it distressed me so much that I excused myself to go to the
bathroom and proceeded to break down sobbing once I got there). I’ve
even considered the possibility that I may be gay, but ruled it out on
account of my not being attracted to girls, at all.

Yeah, I’m really young, and yes, I too roll my eyes nearly audibly
whenever I hear other 19-year-olds mourning their lost love and
whining, “I’ll never feel that way about anyone ever again!” I don’t
know why I should be any different, but hey, you were nineteen (and a
half!) once, you must remember what it’s like to think that no one in
the world understands how you feel. My friends all tell me that I’m
being ridiculous, and when I think about it logically I know that
they’re right, but my friends are all my age and know even less about
love than I do.

I guess that’s what I’m hoping you can help me with. You, presumably,
have been through all of this: can you please reassure me that I’m just
being a big stupid idiot when I think that this is as good as it gets
and that I’m never going to fall in love again?

In Search of a Good Slap Upside the Head

I’ve got a question of etiquette for you. A group of friends and I went to a concert two weekends ago. One person, Brian, was in charge of getting all the tickets, and we each settled individually with him how to pay him back.

At the concert, Brian got very, very drunk. This wasn’t a big deal (we’re college students…public drunkenness, while obnoxious, is more or less par for the course); we all took care of him and still had a great time. Cut to this past week, when I tried to pay him back for my ticket. He refuses to accept money from me, claiming that he “ruined everyone’s night” and that he would feel wrong taking the money after we had to take care of him. First off, he certainly didn’t ruin my night or anyone else’s and has nothing to make up for. Second, everyone else has already paid. If he wouldn’t take money from anyone, I’d still think he was being silly, but it’s unfair to the whole group if I’m the only one that doesn’t pay.

I’ve tried to tell him how I feel about all this, but he won’t budge. This whole thing has become a real source of tension; as things stand, he’s insulted that I won’t accept his way of making up to me, and I’m ticked that he’s putting me in a really awkward position, and around and around we go.

So what’s the best thing to do here? I can’t keep the money, but I can’t get him to take it, either. Do I leave the money under his pillow? Do I write a check so he can cash it or tear it up as he chooses? Do I take him out to one heck of a nice dinner and call it even?

Money and Drink Are the Roots of All Evil…

Friend is dating Boy. Love abounds. They, to put it bluntly, love their sex.
One day, Friend gets it into her head that Friend and Boy should share
sexual histories. Apparently, Boy = man-whore (understandably. Boy is
GORGEOUS). Boy has had more sexual partners than Friend has. By about a 5:1
margin.

This worries Friend. Friend is SO worried about Boy’s skankery that
she worries over it incessantly. It becomes everything she talks about. To
alleviate her panic, Boy volunteers to get tested for every STD on the
books. He comes back clean, but Friend is unsatisfied and whines to me
(Friend tells me everything) about various bumps. I begin to be repulsed,
but I still understand about her worries — Friend, understandably, has no
desire to contract herpes or warts. Unfortunately, Friend goes into great
detail about these bumps. And…consistency. And inspection of…lots of
body parts.

Here’s my problem: I’m pretty sure, at this point, that I could draw models
of both Boy’s and Friend’s genitalia. I don’t want to be able to do this. I
don’t want to hear any more about any of it, but I don’t want to give Friend
the impression that I don’t care — I do. I’ve been there since the conception
(hee!) of this relationship, and I want to be there if it ends. The thing
is, I don’t want to hear about self-exams, genital bumps, and more.

It’s not that she’s sensitive and easily offended, or she won’t stop if I
ask her, but I really don’t think that I want to confront her directly about
this — despite the obvious lack of decorum involved in these conversation, I
would like to ask her to stop with some modicum of good taste. Obviously my
coming out and saying, “I don’t want to hear about your twat and his dick
anymore. Stop it. Now!” isn’t going to cut it.

Help!

It can’t be healthy to be bleaching my brain just to get the images out

My boyfriend of four years, “T,” with whom I have been living for one year,
is (and has been, for as long as we’ve been dating), having a major identity
crisis. And I have too, I suppose — it’s natural. We’re both in our
mid-twenties with college degrees but unsure as to what paths to take.

During our relationship, he has often talked about changing career fields,
moving away (to bigger cities or overseas), starting his own business, and
various other propositions. T is a highly creative person who has dabbled
in lots of mediums (doing most of them quite well). He recently decided to
focus his efforts on music (rather than film, his college major and job
experience) — becoming a recording engineer and playing in a band.

Although I love T with every ounce of my being and of course I want him to
succeed and be happy, I have to admit that I’ve always seized up a little as
he talks about changing course, because I suspected his future plans
wouldn’t include me.

Now that day has come. With a lot of ambivalence, he got a job at, and then
got unfairly fired by, a local film company which he put a lot of eggs in one
basket for, so to speak. Then T went through a brief but
savings-account-sucking period of unemployment. Now he has decided that his
best option is to move back in with his parents (who live in another state)
after being on his own for eight years, in order to save enough money so he
can spend next summer overseas recording an album with some of his musician
friends.

He says he has no choice in the matter; that because of his unemployment,
and in order to take advantage of this album-recording opportunity, he
absolutely needs to get a job and save serious cash, which is certainly
easier when living rent-free under one’s parents’ roof. He absolutely
could, though, get a decent job here and keep living with me, but he would
just have to try a hell of a lot harder to budget and maybe make some
sacrifices. Also: an album can be recorded anywhere, like for instance in
the studio he has spent A LOT of money building in our very own apartment.

But he’s going. I will miss him horribly, because he’s the most loyal,
sexy, dynamic, fascinating man I’ve ever met. We have been through a lot
and come quite far. But unfortunately, this situation sheds light on one
thing I would rather ignore about our relationship, specifically the
question of whether it is going anywhere (I don’t necessarily want marriage,
but I would like some kind of commitment and I would love to make plans for
the future with him).

My mother, whose advice I trust (although she is a bit reactionary), thinks
his plans are ultra-flaky and that if T really loved me, “he’d put a ring on
my finger before he went off to ‘do what he needs to do.'” I think that’s a bit much, but I kind of agree that some kind of
understanding should be reached before he moves away; in order to make a
long-distance relationship work it is usually assumed that the parties
involved will come back together in the future. Right?

T has basically refused to discuss what the future holds, claiming that “he
needs to figure his own shit out first.” It seems like he wants to stay
together indefinitely until it is convenient for him to make a decision
about Us, or maybe it’s just not that important to him because his
priorities are elsewhere.

Do you think his refusal to commit now is due to his in-flux situation, or
is it about avoiding the truth? Is it fair to demand some kind of
understanding before he leaves? I desperately want to make peace with the
fact that he’s leaving and support his decision. I understand his need for
adventure and a change of pace, and the last thing I want to do is make him
feel trapped (’cause that will really make him run away), but I also feel a
lack of control that’s making me feel crazy and sad.

Yours,
Solitary Sleeper-To-Be