At age 30, I suddenly find myself horny as hell, single as can be, and having constant sexual fantasies about a man I had my one and only one-night stand with about nine months ago.

My sexual history is far less extensive than that of the typical female my age. To make a long story short, I didn’t date at all in high school or college. I was socially awkward, and, in retrospect, clinically depressed. This combination, not surprisingly, did not make me particularly popular with the opposite sex.

Fortunately, things improved to some extent after college. In my early twenties, I had a longterm (approximately two years) relationship with a guy who was smart, sweet, caring — and impotent. I was a virgin who didn’t know how to help him with his problem, he was a virgin who didn’t feel comfortable talking about it and said it was partially my fault because he sensed that I was somewhat ambivalent about having sex with him and it made him unable to perform. We did other sexual things, but never had intercourse. It was one of the many reasons we broke up. After our relationship ended, I carried around a lot of anxiety about sex. I felt very unattractive, like the sight of my naked body would repulse a man. I recognized that my feelings were irrational, but that didn’t make them go away. I dated very rarely, having never really gotten over my social awkwardness, and never had sex.

About a year ago, I met One Night Stand at a party. Unlike the Comic Book Geek/Fan Boys that I usually attract, he was a very successful businessman. He hit on me very directly, which was a new experience for me. We ended up getting into an argument about something stupid, and ended our conversation. For whatever reason, I couldn’t get him out of my head, and about a month and a half later, I finally got up the courage to call him. (Again, I am a social retard.) I psyched my up by saying to myself, “Hey, this is going to go one of two ways: either you’ll make plans to meet for a drink sometime, or he’ll reject you — and you’ll never see him again, so it won’t matter. It’s not like he’s going to invite you to come over to his place for a night of sex.” Actually, that’s exactly what he did, and, in part because I was amused that my little mental pep talk was so offbase, I agreed.

The experience was rather bizarre. I felt incredibly sexy, doing something so out of character for me. And he really seemed to like my body — a whole lot — he emphatically stated that he preferred short, flat-chested women like me to the multitudes of women with enormous implants who populate our city, which really boosted my confidence. I opened up to him about feeling like I hadn’t achieved any of my professional goals. It was very interesting talking to someone who had succeeded beyond my wildest dreams — kind of like hooking up with a younger Donald Trump minus the bad hair and the gold leaf furniture. He actually had some very good advice.

I told him that this wasn’t the sort of thing that I usually did — but I was too embarrassed to tell him I was technically a virgin. Casual sex was clearly not a new experience for him. The end result was me lying there rather passively and not effectively communicating what I wanted, which meant the sex wasn’t particularly pleasurable for me. I hold myself responsible for this. I don’t expect a near stranger to psychically sense my sexual history. Afterwards he said that this didn’t have to be a one night thing and encouraged me to keep in touch. I was mentally weirded out, thinking, “Oh my God. I just lost my virginity to a guy I barely know,” and covered by acting very blase, which I’m sure he interpreted as disinterest. He never called me again. I never called him, either.

Ever since that night, my life has improved dramatically. I have drawn on the experience as a source of strength, “Hey, you pulled off a one-night stand — you can do anything.” I now have my dream job, my income has more than doubled, and I am no longer afraid of men. While on vacation, I ended up hooking up with a rather hot guy from Italy. I shed what was left of my inhibitions with him, and had a very good sexual experience — although, due to lack of condoms, we didn’t have sex in the Bill Clinton technical sense.

For the past few weeks, I have been thinking constantly of One-Night Stand. I think I would like to embark on a “fuckbuddy” type relationship with him. I really want to explore my sexuality, and, with no potential boyfriends on the horizon, this seems like the best way to do it. My questions are: A) Is it possible to call someone you had a one-night stand with nearly a year later without coming across as psycho, and if so, how do you do it? B) How does one go about asking for such a relationship?

I realize that there’s every possibility he’s dating someone now, or disinterested for other reasons, but I’d like to give it a shot. If nothing else, taking the emotional risk of asking might be good for me. Despite my newfound confidence, I’m still really lousy at calling guys on the phone and am unsure what to say. I also recognize that sleeping with him was a very significant experience for me, but meant absolutely nothing to him. I’m sure I have rarely, if ever, crossed his mind in the past year, and that he has probably been involved with many other women. I am okay with this. But I also recognize that my lack of experience might make me a bad candidate for this sort of relationship. I might end up becoming overly emotionally involved. Do you think I could be setting myself up for disaster?

Thanks for letting me ramble on. I always enjoy your insightful advice.

Sincerely,
Late Bloomer

I read your advice column regularly and you always give very sound advice that I totally agree with, and so now I actually have a question for you! It’s really just an etiquette question, nothing really major, but I’m at a loss here and was hoping you could help me out.

I’m getting married this year. Couldn’t be happier about that — he’s the best guy in the world, we’re totally thrilled, blah blah blah mushiness. That’s not the problem. The problem is I have a question about my guest list.

I work at a pretty regular-sized company. But my department is just me, my boss, and one other person. The one other person lives and works on the other coast, and so is never in my office. I’ve met her once due to a business trip but speak to her five or six times a day, since we all work together very closely. So we’re in constant contact. I get along very well with her and like her very much, both personally and professionally. I also get along great with my boss, love him, and of course, due to etiquette reasons (and also the fact that I honestly really like him), am planning to invite him to my wedding. As I understand it, you’re supposed to invite your boss as a courtesy anyway.

The question is, do we invite the other person on my team to the wedding? I know that typically it’s standard only really to invite bosses, and that a lot of people shy away from inviting regular co-workers who aren’t also personal friends — because then you run into the whole having-to-invite-everyone-so-that-you-don’t-offend-people-by-leaving-them-out thing. But since our team is only three people, I really wouldn’t offend anyone else in the office by inviting her. But I’m worried — do I risk potentially offending HER by not inviting her, since she’s the only one I’m leaving out?

Our guest list is already over 200 people, Sars, and it’s going to be tight to make it any smaller — the pre-husband and I are over our limit of guests already. But I’m figuring that she and her husband live on the other side of the country, so they probably wouldn’t come anyway, and it would be more of a courtesy thing to extend an invitation, right? Or am I wrong about that? People tend to surprise you and travel far distances for weddings, and I really would be thrilled to have her there, if she could make it. But I’m really not friends with her, it’s just a question of etiquette and expense.

What do I do?

Dammit, this cost per head thing is KILLING me!!

Long-time reader, first-time writer — and looking for some of your excellent advice about a tricky work situation. I work for a fairly small company, just 50 people in my office, and so we all know each other pretty well. I have a colleague/friend — let’s call her E — who split up with her long-term boyfriend a few months ago. Since then, I’ve seen her in the company of another colleague (A) a couple of times. Nothing unusual really, but I just had a gut feeling that something was going on. I subsequently told my boyfriend (and fellow colleague) about my suspicions and he confirmed them, saying that he’d heard a rumor from a former colleague/close friend but hadn’t said anything because he hadn’t wanted me to be upset, given that I like both E and A. Why should I be upset, you cry? A is, of course, married, with kids.

Now, I know this isn’t any of my business. However, we do work for a small company and if I’ve noticed and put two and two together, other people will. Should I mention to E that I’ve worked it out and that she and A should be more careful? Should I say nothing? I’d just hate to see her professional reputation suffer if the gossip spreads. And how can I make sure my boyfriend tells me this sort of thing in the future? Good work gossip can be so hard to find!

Yours,
I Thought Discretion Used To Be The Better Part Of Valor

This is somewhere between a usage question and a manners question, so I’m hoping it’s up your alley.

My question involves what to call my husband’s sister’s husband when I’m introducing him or referring to him. I seem to remember reading somewhere that he is not properly referred to as my brother-in-law; he’s my husband’s brother-in-law, but not mine.

If he’s with his wife, it’s easy: “This is my sister-in-law Beth, and this is her husband John.” But when he’s alone, it sounds awkward to say “This is my sister-in-law’s husband,” or, “This is my husband’s brother-in-law,” or, “This is some dude who married into the same family I did,” or whatever. Is there a less tongue-twisty way to get this concept across that I’m missing? Or is “brother-in-law,” though not technically correct, the best choice in this situation just for the sake of simplicity?

Thanks,
John’s Wife’s Brother’s Wife

What do you do when your roommate’s a bigot?

My roommate Princess is a bit of a rich-girl brat, but there’s a bit of that in many people I do like, so I suppose it’s forgivable. She’s not one of my favorite people for a number of reasons, but the current main problem is that her particular brand of snobbery looks down on, well, minorities and lower socioeconomic classes.

She’s fucked up in any number of ways, almost all due to her parents being permissive but crazy, and not a little snobby themselves, but I’d say, in my “freshman psych rears its ugly head” way, that the prejudice part stems from being the daughter of a real estate magnate in an economically depressed city, therefore having a natural resentment of minorities and poor people, who drive the real estate values down further, decreasing Daddy’s profits, and preventing said daughter from being kept in the style to which she is accustomed (read: one fewer pair of Theory pants a week).

Okay. Fine. You can’t stop anyone from having their prejudices, et cetera et cetera, and she’s fucked up, not evil, as my mother is fond of contending.

But how do you handle it when she says racist and bigoted things in the course of a conversation? I mean, this is not a once-in-a-while occurrence; she’s prone to linking obesity (the cardinal sin in her mind; she’s got food issues, too) with the lower economic classes, because “those people are so much more, like, irresponsible, and they don’t take care of themselves, y’know?” But one of the more egregious things she’s said lately was a conversation that went as follows:

Other Roommate walks into common room.

Princess: Oh my god, Other Roommate, this girl in my English class used the word “conversate” today.

Other Roommate: (confused, not sensing the reason for the apparent outrage) Um…is that…a verb?

Princess: It is if you’re black.

Other Roommate: (at a loss) Um…is she black?

Princess: (smiles, raises eyebrow) Uh, yeah?

End scene.

I talked to said Other Roommate about this, and she nearly tore her hair out trying to think of what she could possibly say to Princess, but settled on nothing, because when Princess is mad at you, it’s very clear, and very unpleasant. But rest assured that this behavior makes all of the other roommates absolutely shriek when they hear about it. Nobody thinks it’s okay.

So I talked to my mom, who works for a “promote acceptance of others” non-profit, and she said that official protocol would dictate that I should just very clearly and calmly tell Princess, when she makes racist remarks, that I don’t appreciate comments like that. I think that’s more likely to get her back up, and I think that the proper response should be more along the lines of “eyes get big, laugh really loudly, and make like what she said was so completely outrageous that she actually has to be kidding, and therefore, treat it like a big joke.” I think that’s a better way to respond, because then I’m giving Princess an out, while still letting her know that it’s a completely inappropriate thing to say.

Any thoughts, Sars? How do you call a roommate on racist comments and keep the relative peace? Is my approach good, or am I just justifying a way to laugh at/embarrass her? And I guess as a related issue, any thoughts as to how you get to the ripe old age of 20, call yourself a liberal Democrat, and think it’s okay to say things like that?

Signed,
She Has Got To Be Kidding Me