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slides: The Best of Dear John 2012

Tuesday, January 01, 2013

 

With the New Year upon is, it's time to round up the very best--the weirdest, funniest, and most provocative--letters to Dear John of 2012.





 

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Teacher's Pet?

Dear John,
 
It’s okay to ask my son’s teacher out, right? No unwritten rule against that, is there? I am a single dad, and I’ve had a couple of conferences with her (my son is in third grade), and I must admit to being quite smitten. I’ve dated enough and it’s rare that I meet someone who interests me, but she does. I don’t know anything about her personal life, but she doesn’t wear a wedding or engagement ring, so that’s enough for me! Am I right?
 
Signed,
Teacher’s Pet, Maybe

Read John's answer, here.

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Affair Spotting?

Dear John,

I work part-time as a waitress at a nice restaurant. It was only my second or third week there when, surprise, I saw a neighbor of mine having a nice, seemingly romantic dinner with a woman who wasn’t his wife. The impression I got was that this was definitely not a business dinner, let’s put it that way. I managed to go unseen by him (as far as I know), but it has bugged me since it happened. (This was a month or so ago.)

I’m wondering if I should tell his wife what I saw. I am not friendly with this couple, but we exchange neighborly pleasantries when we see each other. They both seem nice, although I’m not so sure about him any more. What makes it complicated for me is that I was the clueless wife in this scenario not all that long ago, and when everything blew up on my ex-husband, I found myself wondering, “Why didn’t anyone TELL me?” A lot of people knew what was going on and I felt so humiliated that I was, cliché though it is, the “last to know.” If I could spare someone else that feeling, I would. I’m so unsure if this is the right thing to do, though. Thoughts?
 
Sincerely,
Been There

Read John's answer, here.

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Dating Dad

Dear John,

I’m in my mid 50s and my son is in his mid 30s. We see each other a lot, but we’re not real close. I’ve been divorced from his mother since he was a teenager and I don’t think he’s ever stopped being mad at me for leaving. Long story. Anyway, he was dating a woman that I had a chance to meet at a couple of family functions, but I don’t think it was too serious between the two of them and I have come to find out that they’re not seeing each other any more. I’m not with anyone either, and truth be told, I rarely meet anyone I’m interested in. I got to know this lady pretty well the couple of times I saw her, though, and we just seemed to hit it off. So I’m thinking of asking her out. She was about midway in age between my son and me, so it’s not like there’s a big age difference there. I mentioned this to a buddy of mine, though, and he thought it was a bad idea, which to be honest, I didn’t expect. So now I’m wondering if he’s right and figured it couldn’t hurt to ask your opinion. Thank you.

Sincerely,
All’s Fair?

Read John's answer, here.

Photo: Alex Proimos/flickr

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Loves His Wingman's Girl

Dear John,
 
I am totally in love with my best friend’s girlfriend. Cliché, right? I’m in my late 20s and I’ve known my best friend since I was a little kid. A couple of years ago he introduced me to his new girlfriend. She seemed fine.

Since then, though, they’ve had their share of ups and downs and when they’re in the middle of one of the downs, I’m the one they confide in or vent to.  Getting to know her this way, though, I have fallen for her hard. And now I don’t feel like I can be supportive and if I’m totally honest, I find myself trying to say things I think she wants to hear to make myself look like the guy she wishes my buddy was.

I’m so confused. Do I let her know how I feel, not expecting her to leave him to be together, but just so she knows? I don’t know what to do. I need advice.
 
Sincerely,
Their Friend

Read John's answer, here.

Photo:  zoetnet/flickr

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Bad Sex Match

Dear John,
 
I am a woman in my early twenties. After being in an exclusive relationship for quite a while, my boyfriend and I had sex for the first time a couple of months ago. (First time with each other; not first time ever.)
 
Neither one of us has a lot of sexual experience, but we’ve had enough to know what we like. And so far, our ideas of what constitutes good sex could not be more different. In a nutshell, and without getting too graphic about it, he wants me to do things I don’t want to do, and I want him to do things he finds boring and unadventurous, I guess.

So so far, sex has not been going well for us. I’ve never been in exactly this kind of situation before. What do you do when the two of you are in different places sexually? Should we both do for each other what we’d rather not, or should we both forego something we want? It doesn’t seem fair for one person to accommodate the other without being accommodated in return.

Adding to this problem is that we’re both very shy and find it hard to talk extremely frankly about these things, but the good news there is we’re getting better at getting the words out, at least? Any suggestions?
 
Sincerely,
Twin Beds

Read John's answer, here.

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Oral Arguments

Dear John,
 
I’m in a relationship that is going well. We’re both in our early thirties and neither one of us has a very extensive history of relationships. To make a long story short, neither one of us had any experience with oral sex and we wanted to give it a try so we did. He really enjoyed receiving it and I liked how much he enjoyed it, so that made it enjoyable for me, too.

But when the roles were reversed, he gave it a minimal effort before deciding that he just couldn’t do it. He found as thoughtful a way as he could to express that he thought it was really gross. But now he still expects it from me. He’s under the impression that I enjoy doing it (I don’t mind, but I could take it or leave it) but now I feel like when I do that without any attempt at reciprocation, I’m being taken advantage of. I hate to feel like I’m keeping score or something, but I am hurt and annoyed that he expects this to be all taking and no giving and that’s fine with him. The worst part of all this is now that it’s become something of an issue, we’ve ended up having sex a little less often, but I just feel like he’s being really selfish about this. How should we resolve it?
 
Signed,
Give And Take

Read John's answer, here.

Photo credit: socialspice.de/flickr

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Hates Her Kids

Dear John,

I’m a middle-aged guy who’s been seeing a woman I’m crazy about for six months. I’m divorced with no kids and my girlfriend is divorced with two kids, 9 and 12. Two boys. There’s no way to sugar coat this, though: I don’t like the kids. They’re unruly, undisciplined brats. My girlfriend has joint custody with her ex-husband, so they’re around a lot. She has no idea how I really feel – I think I’ve done a good job of hiding it and she thinks her kids hung the moon. She just doesn’t see them objectively. So what do you think? Is there hope for this relationship, or should I cut my losses?

Signed,
I Know Cute and They’re Not It

Read John's answer, here.

Photo: AngryJulieMonday/flickr

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Three's a Crowd

Dear John,
 
My boyfriend wants me to do something I’m ambivalent about: sleep with him and another guy. It’s not quite how it sounds – the “other guy” is a friend of his, and in fact, I dated him briefly a couple of years ago. It was so unserious (although it was sexual), that to say we broke up makes it sound like there was more there than there was. Anyway, we’re all friends, we all get along great, I like them both, find them both attractive, etc., and my boyfriend really wants to try this out.

When I ask him why it’s so important to him, he doesn’t have a reason except that the idea of it is “really hot.” I’m not opposed to it exactly; I’m just not very excited about it. To be honest, and he knows this, the thought of three people having sex together just seems like one too many to me, simple as that.

I know it would make him happy and I do want to do it for him, but I don’t know. I’ve been close to saying okay a couple of times because I’m tired of talking about it. What do you think?
 
Sincerely,
On The Fence

Read John's answer, here.

Photo: Christine Rondeau/flickr

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He Hates Her Hair

Dear John,

My girlfriend just got a new haircut and I hate it! Her long hair was the first thing that attracted me to her, and now she’s gone in the opposite direction. She has a haircut like a boy from the fifties. Ugh, I can’t stand it. I actually feel like I’m not attracted to her any more.

I know it will grow back, but she won’t stop saying how much she likes it! Should I tell her straight up that I don’t like it or hope she gets sick of it or what? I know if she knew how much I don’t like it she’d let it grow out again. Should I see if one of her girlfriends that I’m friends with will let her know it doesn’t look good? I know it seems like a small thing and she’s the same person and everything. But it just looks bad.

Sincerely,

Liked Her Better As A Girl

Read John's answer, here.

Photo: nowhere Zen New Jersey/flickr

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Relationship Barrier

Dear John,
 
I’ve been dating a woman for about six months who seems to have an inordinate fear of std’s. She knows of ones I’ve never even heard of, including symptoms and transmission rates. So she insists I use a condom when we’re intimate. I respect her taking charge of her sexual health, but I feel like this has gone too far. There’s literally no chance she can get pregnant, so that’s not an issue. I have assured her I’ve been tested for std’s and I would gladly get tested again, with her, if it would reassure her everything’s okay. I don’t have any other sex partners and I wouldn’t cheat on her. The thing is, I hate using a condom. I’ve never liked them and about a quarter of the time, wearing a condom ends up making me lose my erection midway through sex. But she refuses to even talk about the possibility of sex without condoms, claiming std testing isn’t perfect, could possibly fail to detect a newly introduced disease, and besides, “Why take the chance?” as she says. It’s the only thing we really don’t see eye to eye on. Any thoughts on how I might get her to loosen up a bit on this?
 
Signed,
Breaking Through The Barrier

Read John's answer, here.

Photo: robertelyov/flickr

 
 

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