To make a long story as short as I can, I have a Boy Problem. No, not THAT kind of boy problem. The Problem Boy is a friend of a very dear friend of mine. Let’s call my friend “Tim” and his friend “Dicksmackbuttfacepants,” or “Bob” for short.

I adore Tim, he’s the first person I met at college, and we’ve been friends a long time. I do not like Bob, but Tim likes him and he’s often around when “our group” hangs out, so we put up with Bob for Tim’s sake. Bob is totally inappropriate, and has to be “funny” and the center of attention at all times.

All of that I can handle. Not a problem. No matter how hard it is for me to understand WHY Tim likes Bob, I’d never ask Tim to choose between us, and neither would anyone else in our group.

So. Problem 1 is that Bob is a ginormous asshat. Lesser Problem 2 is that Tim is always apologizing to us for Bob’s asshat behavior, which just enables the asshattery, but we’re working on that.

Since the Beginning of Time, whenever I’d bring a guy as My Date to a group friend outing, Bob would come up to the guy at some point during the night, sometimes right in front of me and sometimes not, and say, “Hey. Dude. I’ll give you $100 for an hour with your girlfriend.” Gahhhhh! After the first couple of times, I always warned my dates in advance, and most of them either blew him off or ignored him.

But now I have a boyfriend. I thought Bob would quit eventually, since it’s only funny once (or, you know, NEVER…) but he has not stopped. Actually, since the boyfriend and I have been together for almost a year, the price has gone up. Bob now routinely offers my boyfriend $500 for an hour with me.

I…don’t get it, Sars. What. The. HELL??? I mean I get that Bob is poorly socialized and has only the most crude and malformed idea of “humor.” Bob still thinks its hilarious to make prank phone calls, and thinks “dead baby” jokes are GEEEEEEEEEEENIUS! But it’s been a year with the same guy, he does this at least once a month, and he. Will. NOT. STOP!!

Also weirdly he’s never propositioned me directly, as if it’s not even up to me and he might as well be asking my dates “can I borrow your car?” He asks even if he has a girlfriend or date with him! (Women actually date Bob? *shudder*)

I know I probably can’t “make” him stop…I guess I’m just looking for witty responses and deflections for myself, and for my boyfriend who is starting to get a bit uncomfortable with the whole thing. Never seeing him again isn’t an option unless I ditch my entire group of eight closest friends, of which Tim is part, and start over from scratch.

I looked in the library under Dealing With Fuckwits 101, and came up empty.

I need some clear-headed advice, and more desperately, some stinging wit — I have no snark of my own!! Help!

$500 is great, but what are we going to do with the extra 59 minutes and 48 seconds?

I am really thankful for the opportunity to talk this out and although I’d love your advice, I’m hoping that just describing everything will give me some kind of a light bulb moment.

For the past two years I’ve been unhappy. Felt a bit dead inside. Withdrew from life. Maybe I was depressed. Maybe it was belated college angst. I don’t know. Sometimes I look around at all the miserable people and think, we can’t all be depressed, can we? I must just have the wrong perspective and should get over it.

But anyway, I feel like I am finally making progress. I have begun making changes in my life over the past few months. I’ve been taking care of myself, making little adjustments that make things slightly easier, slightly better suited to my natural inclinations; things that make me a little happier. Of course, now I’m a little scared about whether I will ever really be happy. That effortless and peacefully secure state of mind I always had as a kid and a teenager. When having fun didn’t require any calculated plan or disconnect from what was going on in my head and heart. Things are better and keep getting progressively a leeeeetle bit better, but I still generally feel disconnected, and a little fragile.

I know that a job change soon will make a lot of difference (cross your fingers for me, I am very close to getting a new one), but I can’t help but wonder if I’ll never feel all the way healthy. The idea of spending years slowly climbing out of the ditch is, well, depressing. But not as depressing as staying in the ditch for years, I suppose. I guess I’m looking for a little support and maybe some wisdom about staying the course. I think I can do it, but it is tough.

She Whose Thrill Is Gone

I have a problem I’ve been struggling with for a long time, and would
appreciate some wise advice. Short version: my sister-in-law’s a bitch.
Yeah, I know, you’ve never heard this one before.

Long version: my brother and his wife have been married for seven years, and
they have two small kids. My sister-in-law was okay at first, if kind of
uptight and judgmental, but hey, that’s her personality. But over the years
she has got weirder and nastier to us all, to the point where it’s pretty
unbearable. She seems to feel that none of us helps out enough with my
parents (my sister is married with kids and lives a few hours away, my other
brother is single and drops in a few times a week on my parents). My father
suffers from Parkinson’s and dementia and my mum is his full-time carer, but
she copes okay at the moment. My eldest brother, the one with the evil wife,
does a lot of practical stuff for them.

However, he’s always been very
closed-off emotionally with us; we’re not a terribly close family, but we
try to get on, and I get on well with my siblings and my parents.
My sister-in-law is nice as pie to other relations and to her son’s friends’
parents, but to all of us (including, at times, my parents) she’s moody,
cold and monosyllabic. She is openly critical of our choices (she thinks my
sister and I like clothes too much, that our jobs are too easy, et cetera) and if
she does something for my parents when I am around, like she takes us all
out for a drive, she makes comments to me about what an imposition it is and
how one of us should be doing this. Her tone and manner always leave me at a
loss for words, for some reason -= I actually think she has some sort of
mental illness (psychoanalysis: her mother died when she was young and she
halped raise her four younger siblings, and she seems to resent us for still
having our parents and, in her view, not doing enough for them).

She has now stopped talking to me altogether: I discovered this about six
months ago when they came to the area where I live on holiday, and we
arranged to meet up for an afternoon. I took the afternoon off work, got on
a train, only to find that all my conversational gambits to her were met
with either monosyllables or silence. When I asked my brother in private
what was up, he blew it off.

A few weeks ago my sister and I dropped by the house: my brother tried to
talk to both of us but she never addressed a word to me the whole time, and
by now I find being in her company so distressing and difficult to bear that
I went upstairs with the kids and basically hid. Nobody has ever had such an
effect on me, I swear. I like to think I can handle myself, but she seems to
have a psychological grip on me.

The problem has come to a head, as they have invited us (me, my brother, my
parents, my aunt) for a family dinner. I initially point-blank told my mum
I couldn’t face it, but my mum can’t bring herself to cry off (we’re a very
non-confrontational family, and honestly, both my father and mother come
from big families, and everyone has always got on, which I know is sort of
unheard of, so we are clueless about handling this). I eventually emailed my
brother, politely asking if he was sure I was welcome, as I had felt very
unwelcome around them and wondered if I had offended SIL. I emphasised how
hurt I felt, but refrained from criticising her. He responded saying of
course I was welcome and that his wife had been under a lot of pressure at
work, et cetera (total crap, but at least he acknowledged her behaviour).

I have agreed to go, and my mum has promised it will never happen again, but
am honestly dreading it. The best I can hope for is civility, but it’s
already casting a shadow over the day for me, and my parents are terribly
upset by her behaviour. My questions are thusly:

How does one deal with conversation with a person who is borderline rude? Do
you keep asking questions, despite getting practically zero reply, and just
try to wear them down with niceness, or is it better just to avoid
conversation with the person? I have been doing the latter recently but feel
that it is actually a form of mental bullying, and want to devise a strategy
for keeping my self-esteem intact.

Secondly, if it goes badly, I have resolved to confront my brother properly
about it, but am wary of opening up a family feud. I don’t want to cause
more problems, or lose access to my niece and nephew. I know that one can’t
just have a big cathartic rant about one’s grudges, although it’s tempting,
but how does one say, “Hey, your wife’s nuts, and we can’t take it anymore?”
My brother is not a good listener or communicator — should I confront him,
or her?

Sorry this ended up so long: I just don’t have the tools to deal with
nutjobs.

Thanks,
JS

I am a dog person who has happily adopted a kitten. This kitten, who I’ll call “Sweet B,” is completely wonderful in all possible ways except one. She likes to sleep next to me and is nice and quiet once she settles in for the night. Until she wakes up at 5:30 or so and feels the urgent need to lick my face. A lot. While purring loudly.

Sweet B will not be deterred from the early-AM cat-administered facial. I’ve tried putting her on the ground, but she just gets back in bed. I’ve tried hiding my face, but she will lick any exposed portion or crawl under the covers to get at me. If Sweet B were a dog, I would just tell her no, and train her out of it, but my cat-owner friends make it seem like I would be breaking her cute and fuzzy little heart if I disciplined her for “grooming” me. She is very social and would be really unhappy if I kept her out of my room entirely (she follows me around everywhere when I’m home) so that’s not really an option. She has access to food and water at all times, so she’s not trying to get me to feed her. Can you train a kitten not to do this? If so, how? Or do I just need to accept this little habit as my friends suggest and start going to bed earlier?

My Sweet B Has a Little Too Much Love

A hundred unsent Vine letters involving boyfriends, grammar, and unruly cats
aside, I think I’ve finally got an issue pressing enough to beg for your wisdom.

I’m a junior in college, have known I was going to be a writer since I was about
six, and I think I’ve finally reached the point of submission: sizable portfolio of
work, edited to (near) perfection? Check. Copy of Writer’s Market? Check.
But…now what?

I managed to become completely discouraged after talking to a friend who edits
a local literary magazine and he admitted that what he accepts and rejects tends
to be kind of arbitrary (doesn’t like your cover letter? It’s going in the trash). And
on top of that, I’ve got some intense parental pressure going on — “Have you
submitted anything yet? You’re wasting your talent! Writers younger than you
are being published!” I’m starting to feel like time’s ticking away here, even
though I’m only 20. Half of me says, “They’re right, it’s never too soon to get
started,” and the other half says it would be smarter to wait a while and get all
the experience I can before facing imminent rejection.

Suddenly I’m overwhelmed by the whole issue. What to send, and where? Which
publications are more likely to accept writers just starting out? Can/should I
send the same story to multiple places? Or multiple stories to the same place?
What in the WORLD goes in a cover letter? I know rejection happens and I’ll have
to face it, but how do you up your chances? And how do you deal with all that
rejection in the meantime?

I know I’m asking a lot here, but any advice you have for a very nervous first-
time writer would be much appreciated!

Thanks,
The next person to ask if I want to be the next Patricia Cornwell gets a fork to
the forehead