I have an embarrassing quandary for you that I have mentioned to no one else.
I’m afraid my boyfriend is gay.

Back story: Tom and I met four and a half years ago, when I was a senior in
college and he was just starting out as a student at our state university
(he’s my age, but dicked around in community college for a few years). We
dated for six months, and then I decided, having graduated, to move to the
big city and be happy. Tom dumped me right before I left, and I chalked it
up to not wanting a long-distance relationship. A year later, we got back
together. This time we lasted about nine months, and this time we were
long-distance. Unsurprisingly, I met someone else, broke it off with Tom,
and vowed never to look back.

Tom spent about a month trying to win me
back — he called me constantly, sent me gifts, cried, told me he loved me for
the first time ever, volunteered to visit my family over the holidays — and I
turned him down; he hadn’t done any of these kind, sensitive things when we
were an actual couple, and I was sick of being taken for granted.
It turned out that my new boyfriend was an abusive alcoholic (awesome!), so
that ended. A few months later, guess who I called after a night of
drinking? Tom. He came to visit, we got back together, and six months later
we moved in together.

Okay. So Tom really is a wonderful guy, despite the long and frustrating
spells of immaturity that I had to put up with for years. He is, quite
simply, a really good person. He respects me, loves me, is always there for
me, makes me laugh, yadda yadda yadda. I am mostly happy. But ever since we
moved in together, I’ve had this nagging feeling that Tom is gay. Why? Well,
for starters, he talks about it a lot — gay men, I mean. He’s always
pointing out people on TV who “look gay” or how pro wrestling looks like a
“big gay orgy.” He makes jokes like “this movie is making ME question my
sexuality” and “I don’t want to go pee in the bushes because what if a
little boy sees me and becomes gay.” Uh…okay, I realize this is making him
sound stupid. I grew up with male friends and I know how guys can get when
they’re around each other — even the smartest, liberal-est, most educated of
them. They make gay jokes. They call each other gay. But Tom seems to bring
it up a LOT, and with me, not his blockhead buddies. He has no gay friends,
but I do, and of course he doesn’t have a problem with them. None of his
comments can ever be classified as hateful, but they could be construed as
homophobic — they’re good-natured, but full of stereotypes.

He’s never kissed or done anything with another man, as far as I know, but
he has a horrible history with women. He was a serial dater and a bit of a
slut in college, and claims that I am the only woman who doesn’t drive him
crazy. He has no female friends. And as for our sex life — it’s okay. When we
were in a long-distance relationship, we would do it, like, ten times in one
weekend. Now it’s down to a couple of times a week (if that). Sure, that
could just be the natural progression of cohabitational sex, or it could be
a manifestation of other issues within our relationship. But couple that
with Tom’s near-obsession with gay men, and I start to get nervous. He
hasn’t exactly grown up in the most welcoming of environments — his parents
are immigrants and we live in the blue-collar area he grew up in — so who’s
to say he’s ever had the chance to entertain the idea?

I know I haven’t illustrated this very well, but the point remains that I’m
aware of something, nervous about it, and terrified to bring it up. Also, I
might just be insecure and a bit crazy. How the hell do I ask my boyfriend
if he’s gay? This totally sucks. Hellllp me Sars.

Unwitting beard?

The problem is that I am suddenly feeling like I need parenting. I see
cousins or just people in general interacting with their parents, and
it hurts. I see people who have the luxury of screwing up and siblings
and parents who help them out when they do and think, wow, they are so
lucky! I see people my age who have completed college on time, and
seem smarter than me and I feel so stupid and inferior. I know that I
do not add up. I’ve always been a huge procrastinator but now it’s
getting worse. Usually, I’ve been able to come through in the last
couple of hours and hand my papers in. Now I have two incompletes.
Tons of backed up stuff to do at work. There is something I really
love about school (including current classes) but I am finding it
harder to pay attention and get assignments done. Work just feels like
a waste, except for my paycheck.

I’ve always been really introverted and never really minded not having
friends. Now, not so much. After all these years of dealing with shit
and being strong and independent, I’m suddenly needy! For parents,
friends, sisters/brothers? This stuff is just the tip of the iceberg
of the other crap that is going on in my head. Am I just supposed to
suck it up since this is all in the past? Am I jealous of people with
parents? I’m not comfortable with that.

Need to get back on the right track

So, after two and a half years of pickiness-induced celibacy at
college, I’ve finally got a guy. We were friends for a semester or so,
and have been dating for about two months — not too long, but we’ve
been seeing each other every day and things have been going better than
I ever could have predicted. He’s brilliant, funny, a great
conversationalist, gush gush et cetera, and he thinks that I’m all of
those things as well. We get along smashingly. There’s only one
problem.

He voted for Bush.

Like 48% of the country I loathe Bush, and I never thought I’d be
dating someone who voted for him (albeit reluctantly). But that isn’t
the problem; I’ve managed to get over it, because said boy is also one
of the most politically astute and rational people I’ve ever met, has
no repugnant views, and while I don’t agree with his choice (and likely
never will), he is more than capable of engaging in civil, principled
debate. I can handle it — debating is one of our favorite pastimes.

No, the problem is that all of my friends — and, more importantly, my
parents — have a blind and vituperative hatred for Bush and everyone
who voted for him. The few friends whom I’ve told about my boyfriend’s
Bush-inclined tendencies have lowered him several notches in their
esteem, and tell me that he must be an idiot and/or an asshole. They
also have warned me not to tell my parents, who read The Nation, listen
to Air America Radio religiously, and have a mini-Dubya with
conflagrating pants hanging in the living room. I get a stomachache
just thinking about it.

Sars, winter break is approaching quickly, and I want him to visit me
at home. Inevitably the parental units will ask about his political
leanings, and I don’t want to lie to them, nor do I want him to lie to
them. I’m actually afraid they’ll throw him out of the house when they
find out. Should I tell them in advance, or will that merely prime them
to hate him? Should I lock them in a room together and let his powers
of eloquent argumentation win them over? How can I get everyone to look
past his somewhat aversive voting record and see that what really
matters is how he treats me — which is gently and lovingly — and how
I feel when I’m with him — which is happy and exceedingly comfortable?
Or am I just deluding myself by saying that’s what really matters?

Guess Who’s Coming to Dinner (But He Likes Clinton!)

Okay, I give up, I am completely conflicted and my friends and family have come
down about 50/50 on both sides of the issue so your help would be greatly
appreciated. I grew up in a small town, a “one grocery store and all the
cashiers know your parents” kind of place. I dated the same guy all the way
through high school and when he graduated two years before me and went to do
a two-year apprenticeship we dated long-distance until he got back.
Unfortunately I was not as happy as everyone else with the relationship and
a year after graduation, despite having valiantly attempted to put up with a
year of my mother’s not so subtle hints about china patterns, I bolted to the
city.

Fast forward two and a half years to the present. I am living in the city
and have been dating the same guy for two years. We are living together and
are planning to get married in the next couple years. Last time we went
home, however, it was a nightmare. Half the town thinks that I betrayed them
by leaving home and my ex-boyfriend, and the other half seems to think that
my new relationship is a “phase” and I will come to my senses, return home
and marry their golden boy any day now. I would happily refuse to return
home and insist that everyone visit me in the city were it not for the fact
that my best friend is getting married in two months.

My friend also happens to be the younger sister of my ex-boyfriend. She
drove ten hours to hand-deliver an invitation to the wedding for both myself
and my boyfriend, and we accepted with only a few reservations. What is
causing my current issue is that in the last few weeks I have been hearing
from my brothers and parents that the mother of the bride is raising all
kinds of hell about my presence. Her last stunt was at the engagement party,
where she spent the entire time telling anyone who would listen that if the
little slut (me, of course) felt entitled to come then there was certainly
nothing that she could do about it. I’d like to be flattered by the fact
that she still seems to pay so much attention to me, but the truth is that I
am hurt by her actions.

My ex-boyfriend and I still talk occasionally, and although we still
disagree on the circumstances under which I left, he now understands why I
needed to go. He has no objections about my attending the wedding. I,
however, no longer wish to attend. I am not looking forward to a week of
snide comments and veiled insults leveled at both myself and my boyfriend.
I’m already aware that close to half of the people at the wedding still
refuse to speak to me. On the other hand I feel trapped because my friend is
counting on my attendance and was quite looking forward to seeing me. Is my
reluctance to attend an immature attempt to get out of an uncomfortable
situation or a legitimate way to avoid conflict?

Signed,
I Don’t

I really don’t know how to even begin to start, so I’ll just jump right in. Thank heavens to the internet for allowing me to ask a question I would find very difficult to say out loud. I’m 24 years old, and a virgin. While I personally have no problem with that, I’m starting to feel that I’ve gotten to an age where that’s a bit strange unless you plan on saving yourself for marriage (which I think is a rather goofy idea myself, but good for people who have those beliefs), which wasn’t really what I planning on.

I have a perfectly ordinary reason for how I ended up skipping a fairly significant event that most people get over in their teens/early 20s. I was diagnosed with a fairly serious disease just after my age hit double digits. Unfortunately the disease in question has major body issues both as a symptom and a side effect of the strongest medications. Major fluctuations in weight all through my teen years — first a size 6, then a few months later up to an 18; down to a size 10, back up to a 20. Suffice to say that I had some serious self-esteem issues related to that, completely aside from the fact that I was seriously ill and in and out of the hospital all of the time.

My unreliable state of health and total lack of self-confidence meant that I didn’t date much at all, I can count on one hand the number of dates I went on in high school with room to spare, and never made it to a second one with anyone. Then after high school I had to take a break while all of my friends left and went to college because I was so sick that it would have been a waste of money since I never would have been in class. That feeling of failure meant that I didn’t get out much. A year or so later, I was healthy enough to work (or thought I was) and start saving for college (medical bills can be amazingly draining to your college fund). I was working with lovely people — who were all about ten years older than me. So not much chance for a social life of any kind there (plus my health was declining again).

A few years later, here I am. Healthier than I’ve been in over a decade, and finally able to have an actual life (the plan is still to pay my way through college at some point), but I feel like I skipped over a few steps. Or I was left behind a few steps, I don’t know. Spending a lot of your childhood in hospitals leads to growing up pretty damn fast — people I’ve only talked to and never met in person usually guess I’m in my mid- to late 30s — or alternately like I never got to grow up so I’m still that gawky confused 12-year-old. It probably makes me feel more awkward because I come off as a fairly conservative person even to my friends, although I don’t really think of myself that way. So have I hit freak status yet? Or just socially delayed? Do I just get it the hell over with, or would any decent guy not give a damn? And if it’s that last one, should I feel it necessary to share how that happened (or more technically, didn’t) or just expect him to not particularly care?

Any opinions or advice would be greatly appreciated.

A convent is starting to look like my only unembarrassing option…