Q: I am a 34-year-old woman. I recently became reacquainted with a boyfriend from college and we write each other daily e-mails. He lives in Alaska and I live on the East Coast. We hadn’t seen each other since 1993. We only broke up then because we were both graduating and headed our separate ways. We have continued our snail-mail and e-mail correspondence on and off for the last 12 years. I always ended it, and he would pursue it again several months later, and I would cave. I usually ended it because of my being seriously involved with other men. Anyway, me and college boy decided it was time to see each other again and got together for five days in New Orleans. We had fabulous sex every night and enjoyed each other’s company all day. Then we parted ways again.
A few days later, I called him and told him I loved him. He said it wasn’t reciprocated. However, he continues to write me daily e-mails. He often tells me he thinks I’m beautiful, sexy, smart, funny, etc. For a guy who’s not interested, he sends some very mixed signals. He claims he was never in love with me, though, and doesn’t think he’ll ever love anyone romantically. Oh yeah — the last person he had sex with before me in New Orleans was me in college. He hadn’t had sex in 12 years! He lives in Alaska and works six to eight months of the year doing remote jobs where he works usually with all men, and often alone. He’s a very rugged, tough, solitary man’s man (and sooooooo sexy). He often asks me to call him and sends me little packages of CDs and DVDs. What do I make of this? He’s already said he’s terrified of my showing up in Alaska and thinks I’m too into him, but then he turns around and tells me there’s nothing wrong with me and he thinks I’m awesome. What do I make of all this? —One Confused Chickie
A: Do you know what the funny thing is about mixed signals, OCC? In most instances mixed signals are actually one loud, clear, unmistakable signal: “I’m a fucking mess! Run! Run! Run!” The reason you can’t decipher the singular signal Alaska Boy is sending you, OCC, is because you’re suffering from a bad case of Wishful Thinking Syndrome (WTS). This man is damaged goods, OCC, but you’re so in love with him that you can’t see him for what he is.
So how do we know he’s damaged goods? Let’s count the ways: For starters he’s a single man who chooses to live in Alaska, which should be renamed the Alaskan National Damaged Goods Refuge. He also says one thing (“I don’t love you, I’ll never love you”) and does another (e-mails, compliments, explosive sex), which is always and everywhere a bad sign. Like a lot of DG men, he wants to feel like he has a girlfriend and/or lover without having to say the words. He also clearly enjoys messing with your head. Run, run, run.
Q: I have these friends. They are married and have a small child. The guy is a great friend of mine. He’s very intelligent, sincere and levelheaded. I could go on and on about him; he is a great person. The woman is probably one of the coolest people I have ever encountered. She’s so sincere and thoughtful. She is also drop-dead gorgeous.
My problem is that I am totally attracted to her and I can’t fight this feeling anymore. We’ve never had a secret meeting or intimate encounter, but it seems like we could. I’ve never acted on my feelings due to the fact that I have been friends with both of them for so long. But when we’re together I always get this vibe from her. We get along great and our conversations always have a flirtatiousness that no one picks up on except for us. What a predicament! There is no telling what could happen. Should I act on this or should I just get a life and find another girl? I’d love to hear some feedback because I can’t share this with any of my friends. —Love or Sex Endangers Resolve
A: Fight this feeling, LOSER. Setting aside the issue of just how scummy it would be to make a pass at a friend’s wife — particularly when the couple has a small child! — nothing in your letter convinced me that this woman is actually attracted to you. You say you detect subtle flirtatious vibes. But are you, admittedly smitten, the best judge? Could there be some other reason why “no one picks up on” this mysterious vibe except you? Could you too be suffering from a bad case of WTS?
Here’s what I suspect is going on: This woman knows how you feel and smiles and nods when you steer the conversation in a flirtatious direction. Why? Because you’re her husband’s friend and she doesn’t want to embarrass you by telling you that she would rather eat her own shit than fuck your vibin’ ass. To spare you the humiliation of hearing those three magic words (“Not gonna happen”), LOSER, she lets you flirt. “Even if I felt the same way he must know nothing can come of this,” she tells herself. “I’m married and a mother and he’s my husband’s friend!” If you were to make the mistake of explicitly hitting on her, LOSER, I promise you she won’t endure you any longer. Nor will her husband. Find another girl.
Q: I am a straight guy, reasonably cute, who in recent months has begun to attract women of a much higher caliber than before. Specifically, I’ve been able to involve myself physically with a very attractive woman I met over the course of job-related travels (call her “A”) while starting to casually date another very attractive woman right here at home (“B”). I want to go back in time 10 years with pictures of these girls and show them to my 16-year-old self.
Soon, Ms. A will be coming to visit for a few days, just as things have begun to move forward with Ms. B. Things are casual enough in both cases that I don’t have any attack of conscience in enjoying A’s company while she’s here (especially since, after she leaves, B is without competition).
But the mind gets to thinking …
While these exceptional women (who are for some reason attracted to me) are both in the same location, perhaps I could up the ante a bit? In short, could I get these two into a threesome? Enjoying the company of two women is something I’ve experienced twice, but I’m worried that trying to get the trifecta here will spoil my chances with both A and B. How can I best use this very narrow window of opportunity? —Heavenly Open Window
A: Does A know about B? Does B know about A? These two details are conspicuously absent from your letter, HOW. If the two hot women know about each other, and it’s an established fact that they don’t mind sharing you, well, then they might be up for a three-way. But if they don’t, well, then we’ve got our third case of WTS in this week’s mailbag. If both of these hot women assume they’re the one and only person you’re seeing at the moment, HOW, letting them know about each other’s existence in the form of a request for a three-way could have disastrous consequences. You could wind up going back in time and showing your 16-year-old self pictures of the hot women you had and lost.Send letters to firstname.lastname@example.org