Sexting Miss Robinson on September 21, 1998…

Dear Breakup Girl,

I’m fifteen, my friend D is fourteen, and Kay is twenty-six. D met Kay online awhile back. She’s rather the party-have-sex-with-everybody type of person, and he and she have had their fair share of cybering/phonesex (she called him; his parents are very strict). Now, I wouldn’t think anything of it, except for the fact that Kay’s birthday is coming up, and D is planning on buying her a gift. However, the gift that he wants for her is a $120 painting (plus shipping). Remember that he’s only fourteen, and he doesn’t even have a steady job. I’m probably just being a friend giving unwanted help, but I wanted to hear your perspective, BG.

— T in Ohio

Dear T,

Okay, yeah, eeeeuw. Belleruth and I struggled a bit with this one.

First, before we get to the creepout part, we concede two things: (1) in BR’s words: “If it doesn’t get weird [too late?], the world being the way it is, a shy, awkward 14-year-old can gently induct himself into the world of sex online without getting too banged around, and avoid diseases too. Also, (2) I can see why he’d want to get her something “big.” He’s probably thinking: “Wow, she’s old, I can’t just buy her, like, a Care Bear. Instead, I’ll buy her an expensive, sexy, soft-black-velvety … painting of the Care Bears. And then have it shipped because it’s too big to schlepp on my Huffy.”

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To Sir with lust on September 21, 1998…

Dear Breakup Girl,

Congratulations on your site. I have a small academic problem for you. I am a graduate student who is perpetually falling for academics/professors — of both genders. I am quite comfortable with the gender part of it, but the academic part causes potential ethical problems, and in my experience, the need to constantly attempt to bridge unwieldy generational boundaries. I am 24, and the objects of my admiration tend to be at least around 35 or over with Captivating Intellects/Teaching Styles. Oh yes, and most already have partners…I am not attracted to people my own age at all, as we generally do not have the same mindset or priorities. Am I Mad? Just Unusual? Destined to spend the rest of my days a lonely young spinster prowling the corridors of the academy? This situation has already caused some emotional strains for me.

Thanking you in anticipation of a reply with footnotes,
— Girl Gradstudent

Dear GG,

You are neither as Mad nor as Unusual as you might like to (¹) think. For one thing, you seem to have good taste. Captivating intellect? Charisma? Good call! You’re off to a better start than the folks who write, “Dear Breakup Girl, The objects of my admiration are all dull as a box of rocks.” For another, you are, um, hardly the first young woman to fall for — or at least be attracted to — sharp, charismatic, Older men (women) who are ultimately unattainable (²). That’s why I think my response to you will apply to everyone out there who has considered — or entered into — an “Inappropriate Relationship.”(³)

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Second thoughts on September 21, 1998…

Dear Breakup Girl,

My boyfriend left for college and I’m a senior in high school….and quite honestly I don’t know what to do. We agreed to stay together because (if I get accepted…and who wouldn’t accept the 4.129 on the ACT student that I am?) chances are I’ll go to the same school as he next year (been interested in it since WAY before we ever met…and he isn’t going there because of me…) and we’ll graduate at the same time (cause I’m taking 4 AP classes and will earn a bunch of college credits from them!) Anyway, problem is, now I’m really lonely and having second thoughts.

I can’t really get out and do that much anyway, I’m spending lots of time studying (because of those four AP classes. And he’s going to school about 12 hours away! So it’s not like I’m going to cheat on him…even though my friends want me to (A**holes.) I really really really love him and swears the same to me. He’s always been good to me, so good to me, he’s so perfect and we think alike and…sigh* But I’m so lonely and unhappy here now. I don’t know if I can live like this for a whole nine months (give or take about two weeks.) It’s just too hard and this IS my senior year. He even told me I could see other people if nothing came of it (does this mean he might do the same? I’m not going to and I really don’t want him to do it. It’s not fair for the other person…leading them on and all, and I don’t think it’s fair for me if he does it either.) (oh yeah, and what if he falls in love with somebody else? What happens to me then?) Truthfully, the only guys I was even slightly interested in ever in the past four years have all either joined the Navy or left for college now. I don’t have that many friends at all…and I just feel like crap. Why’d he have to go to school so far away? I already don’t like this LDR thing, I’ve felt like crying for weeks. Everybody I know says to break up with him–but I’ll even be more alone then. And I need and want his parents help next year when I leave for school (my parents aren’t willing to make that long trip.) He told me not to be sad, so I don’t want to tell him how I feel! But I AM sad, I can’t help it, I don’t know that there is anything else I can ever be! I don’t know if breaking up would help or not, I think not. But I need something! Oh what should I do?

— LDR Gurl

BG goes the distance after the jump!

You say you want a resolution on September 21, 1998…

Dear Breakup Girl,

It’s been just shy of two months since my ex-fiance and I broke up. He’d been cheating on me with some girl from the Internet as a way of avoiding the fact that we weren’t getting along as well as we used to. The relationship was troubled way before Ms. Naughty Chat came along: she was just the catalyst for what I didn’t want to believe was the inevitable. He’d given up on me long before I’d given up on him… he calls it “being further along in the grieving process” which frankly makes me want to puke from all the pop-psychological flavor of the statement.

Despite all that both of us did to f**k things up between us, both of us (really, truly) do want to be friends, because we were actually really good friends before everything fell apart and it would be a waste to not try to get some of that back, even though the romance will never be there again. (I miss him like that, too, but I don’t trust him in that department anymore.)

Part of the problem with this is that I feel that a lot of stuff between us is unresolved… there’s a lot of unanswered questions about why and when and how that he hasn’t answered yet. He says that it’s as answered as it’s going to be (i.e. hardly at all) and that we should try to move on. This reminds me of that ugly-ass statement that floated around in the political world a few years ago: “Now is a time for healing.” Except that politicians only said it after things like the Rodney King verdict and after bombing some country. The implied thing here is “Okay, I know I’ve just punched you in the gut, and you really either want to know why, or punch back, but NOW IS A TIME FOR HEALING, meaning you’ll just have to be a good sport and get over it.”

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Keeping things interesting on September 21, 1998…

Dear Breakup Girl,

Is there something in between having sex and not having sex??? Because if there is, I need to know what it is in order to hang onto a guy after the third date!

See, in December I fell for this guy and we clicked — tons of e-mail, great two dates, great phone conversations, he bought me a plane ticket so I could end my visit home early and see him. Well, he picked me up from the airport, we did the deed, he dumped me over e-mail the next day saying I gave it up too easy.

Gun shy and hurt, I spend the next several months healing, working hard in my profession and building inner-strength. Then last Saturday night I go out with this *great* guy and we have an absolutely fabulous 11 hour date. He couldn’t wait to see me again so we met up the next night. That night he arrives with lips and hands in motion, makes the move, I (learning from the past) ask if we can hold off, he runs. It was like having the Roadrunner exiting my apartment (meep! meep!).

You sleep with a guy — he bolts.

You don’t sleep with a guy — he bolts.

So back to my original question. Is there something between having sex and not having sex where a girl can keep her self-respect AND get to the fourth date?

— Bitten Smitten Kitten

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Finishing last on September 21, 1998…

Dear Breakup Girl,

I’ve been going out with this girl for a while now, and I’ve been hearing rumors that she wants to break up with me. The main problem is that I’ve heard that reason is that she likes this loser who’s known as a “bad boy.” You know the type. Into drugs, sneaking out of the house, heavy drinking, doesn’t say much, doesn’t come to class much… my question is, why do girls always seem to go for the bad guy instead of the good guy?

— Joe

Dear Joe,

I’ve talked about the Nice Guy thing a lot before, cautioning everyone that the opposite of Nice Guy is not Mean Guy; it’s a nice guy who also acts like a boyfriend-guy who’s not “too nice” to ask you out. But about the bad boy thing, yeah, fair enough. For men, it’s the thrill of the chase; for women, it’s the thrill of the … car chase. If you wanna dig into the whole psychology of the phenom, there’s a mildly cheesy but quite informative book called — guess — Bad Boys that can give you some good answers. (If you want to retain any semblance of badness yourself, I’d get a friend to pick it up for you.) I will say this, though: most people assume that we go for the baddies (if/when we do) out of some sort of pathetic zero-self-esteem “Hurt me! Ignore me! You’re right, drugs are more interesting than I am!” impulse. Well, okay, yeah, that’s pretty on the mark. But sometimes, it’s also this misguided faux-noble mission to be the one to — claim to — find the diamond in the roughneck. Or sometimes, you seek out the bad boy to make you look good (though also, granted, dumb) by comparison.

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MSN.com, Match.com, HappenMagazine.com: they’re in a healthy and satisfying 3-way relationship. Meaning that you can find MSN/Match.com’s “Ask Lynn” columns –penned by BG’s alter ego — over at Happen now as well.

This week Lynn helps Frozen-with-fear Phil who has gotten plenty of first dates, but is baffled when it comes to making the next move:

Is a tie too much, or will I look over-dressed? Should I touch my date’s arm, her shoulder… or not touch her at all? When is it OK to talk about certain subjects? Do I wait for the awkward moment at the end of the date for a kiss or not? These are just a few of the thousands of questions that go through my head. I don’t know what to do about any of it, and it’s making me sick.

Read the full letter at Happen Magazine for some ground rules from Lynn. Then come back here and add your own suggestions in the comments below!

Loving too much on September 21, 1998…

Dear Breakup Girl,

How many times do you think a woman should get divorced before she should begin to question the validity of her choice to continually get married? Do you think women should start to re-think the whole marriage idea after two divorces? Four? Five? Or do you feel that as long as the woman is happy going from marriage to marriage, she should do so, regardless of what she does to her reputation, her children, and those men she leaves behind? Is marrying a right, to be exercised as you please, or is it more of a responsibility, especially after multiple divorces? Should society simply turn a blind eye to women who marry time and time again, only to divorce a year or two later to start again? Or should someone (for example, a Super Heroine who specializes in breakups) start some sort of therapy group for women who unceasingly seek marriage, only to seek divorce? Thanks.

— Crazy Doug

Dear Crazy Doug,

How many questions do you have to ask Breakup Girl before she realizes they aren’t entirely hypothetical?

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No way out on September 21, 1998…

Dear Breakup Girl,

I have been with the same person for 2 and a half years now, and things have been really good–the best I’ve ever had. However, since I’m 25, and most of my friends are around that age too, the big topic/issue/event of this past summer should be obvious–yup, weddings. Goin’ to ’em, bein’ in ’em, bridal showers, engagement parties, flowers, dresses everything. Luckily, it’s mainly “other” people, not close friends. (A co-worker; my best friend’s old high school chum; the son of some of my parents’ friends, etc.)

But—and this is an important but—it is driving me absolutely insane. Normally a reasonable and logical person, I am finding myself alternating between renting movies or surfing web sites or talking to engaged people, basically doing having to do with weddings OR feeling the urge to dump my boyfriend, quit my job, and flee the country. Hike around Europe by myself, work in a coffee shop, basically pretend I’m still 19. Or pick up guys in some random bar. Something. Anything but wearing white. All of which would be fine if it weren’t for the dreams. Yup. Normally sane me has been having terrible anxiety dreams where I get married but I don’t want to, where my boyfriend catches me kissing other guys, everything. I want to marry this guy, eventually. Maybe even in a year or two. I just want to stop being bombarded by this whole mudslide of marriage details while I’m trying to figure out my own life. (And yes, I know, the magazines/movies/stores have always been there, I just never noticed.)

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The most heart-warming — and geekiest — internet proposal yesterday had to be the mashable employee who proposed to his girlfriend via infographic. If you loved that story like we did, check out DVICE’s rundown of 5 nerdy ways geeks are popping the question as well as their earlier Top 10 geeky proposals of 2011.