Let’s wrap on December 29, 1997…

Dear Breakup Girl,

What should I get my boyfriend for Christmas? We have been only going out for a month but we are serious.

— Michelle

Dear Michelle,

Well, missy, if you’ve been going out for only a month, then Breakup Girl knows this guy about as well as you do. But your letter does highlight a common problem: meeting someone just before a major gift-giving holiday. There’s also the less common (but perhaps more serious) problem of meeting someone just before a non-gift-giving holiday, and giving him something anyway — planting a tree in his honor on Arbor Day, for example.

(more…)

Virgin/merry from December 29, 1997…

Dear Breakup Girl,

This Christmas I’ve been naughty AND nice. Two problems plague this romantic heart. I’ve been “nice” and supportive of an internet friend for two years now, the shoulder and the punching bag through thick and thin and foggy. We’ve met, declared long distance love on the eve and morn of our virginity, and been hunky-dory up till the twelve days before Christmas. But now the stuffing in my stocking is in another the-world-hates-me spin. My patience wears thin.

Now your favorite, the “naughty.” She’s 17, I’m 26 [you sigh here]. Girlfriends have been very rare on the granted end of my wish list (see: 26, virgin until recently) and the charm of this first girl only just began to wear thin/thick. Until now it’s been two kindred souls gulfed only by age and distance. I know my patience will be rewarded if I can only get back into the spirit of past, present and future, but it’s so difficult sometimes loving someone through monosyllables and gloomy glums. Time and experience will solve our yule-tide blues, but what can this elf do in-between seasons?

— Mikey Pooh in Missouri

(more…)

Repeating themselves on December 29, 1997…

Dear Breakup Girl,

For two years in a row I have been dumped on December 1 (true fact). Do you think the secret for me is to find love is to skip town next time 12/1 comes around?

–Dumped in December

Dear Dumped in December,

Skipping town will not help. December 1 is recognized – internationally and historically – as (and here’s Breakup Girl’s positive spin) a day of independence.

On that day in history:
(1640) Portugal regains independence after 60 years of Spanish rule
(1821) Santo Domingo (Dominican Republic) declares independence from Spain
(1918) Iceland becomes independent state under the Danish crown
(1973) Australia grants self-government to Papua New Guinea
(1978) President Carter more than doubles national park system size (“needed space”)
(1991) Ukrainian people vote for independence
(1997) Dumped in December writes to Breakup Girl

The best I can tell you is next time – and yeah, buddy, these things come in threes — check Any-Day-In History to determine how your breakup actually fits into a grand historical timeline. You might also find some solace in the fact that your ex shares a birthday with, say, Mussolini, or Charo.

Love,
Breakup Girl

Home from college on December 22, 1997…

Dear Breakup Girl,

My now-ex-girlfriend and I broke up two weeks after I left for college. She is in high school and said that she didn’t feel she could wait for me and watch her senior year pass her by. She is very popular and gets many guys but both she and I know that I’m the one she was happy with.

We went out for a year and I couldn’t believe she now just wanted to date. It has now been about two months since we broke up and a month since I’ve talked to her. She never was one to express herself. But I still seem to want her back. Can I get her back? Should I get her back? Should I talk to her over Christmas break or just continue wondering how she feels? Please help me.

— Can’t Let Go

(more…)

Naughty thoughts from December 22, 1997…

Dear Breakup Girl,

I have been planning to break up with my boyfriend (of two months) but would rather wait until after the first of the year. My decision (based on my desire to see other guys, coupled with his irresponsibility and general disorganization) has been delayed because of the holidays and, more importantly, the fact that we both have two weeks of difficult final exams. If I know that he bought me an expensive Christmas present, am I under any obligation to stay with him or to return the gift to him after we break up? Is the fact that the gift is something I lobbied for extensively in a previous relationship — but never got — material to this question at all?

— Merry Christmas

(more…)

A Christmas conundrum from December 16, 1997…

Dear Breakup Girl,
Thanks for being there at just the right time. My boyfriend of 5-1/2 years just broke up with me a week and a half ago. In Christmases past, I’ve been used to sending and receiving cards to/from “K & P.” Now I’m dreading the fact that I have to somehow tell all of these people that he and I are no longer together (when it was generally assumed that we would be together forever). It still hurts to talk about it…how can I tell people about us without making the whole card thing a big bummer?
— Just K

(more…)

The winter holidays can be a tough time of year whether or not there’s a dependent Claus in your life. It’s hard to be single at Yuletide, because for one thing, you have to hear your parents say things like, “Won’t your friend be joining us this year?” and “Well, did you sit with anyone interesting on the train?” and “Are you sure you have a good dermatologist?” It’s also hard to be in a couple at the holidays, because it’s … expensive. What to do? How much to spend? Where to kiss? What is wassail? Here’s Breakup Girl’s mini-FAQ…

Should I buy my new boyfriend/girlfriend a holiday present?

Ah, a common problem: meeting someone just before a major gift-giving holiday. (There’s also the less common — but perhaps more serious — problem of meeting someone just before a non-gift-giving holiday, and giving him something anyway — planting a tree in his honor on Arbor Day, for example. )

So here’s the rule of thumb: at the early stage, your presents should not be commanding. In other words,
DO: pick up a little something sweet, warm, or fuzzy — chocolate, mittens, dice — that says “Hey there, I think you’re kinda sweet, warm, and fuzzy.”
DON’T regale him with anything time-consuming, grand, or intimidating — a ten-course dinner, a romantic weekend at a B&B, a mortgage — that says “Sit here, stay here, sign here.” Give someone new that kind of Christmas gift, and I give your relationship, oh, 12 days.

(more…)

Dealing with nice guys on January 19, 1998…

Dear Breakup Girl,
How do I tell a guy-friend that I’m not interested in him romantically without using that awful cliché, “I like you, but only as a friend.”? I know guys hate to hear that phrase.
— Katherine

Dear Katherine,
You are absolutely right. Say anything but. I mean, if you’re going to say that, heck, you might as well say, “You’ve always been sort of a Richard Simmons figure in my life.” This is one of the rare scenarios where Breakup Girl does advocate telling an itty bitty dignity-preserving white lie. Seriously. Tell him you’re not interested, tell him you’re interested in someone else, tell him you’re in love with The Lord … just do not use the word “friend.” (Or, for that matter, “nice.”) If you don’t believe me, read the next letter.
Love,
Breakup Girl

Today we present the original “loft-builder” letter from January 19, 1998, which inspired Paul The Intern’s origin as well as this classic animation!

Dear Breakup Girl,

The thing I fear most in life is “I just want to be friends.” Or “I don’t want to ruin our friendship with a relationship now.”

I have been trying to get to know these women in college. I did all the things a “nice guy” does. I helped move big stuff into their dorm rooms, set up computers and bed lofts, what have you. That’s how I am: When I like a woman, I try to help her out. Well…then I get to be her best friend. I’ve tried not to be a “nice guy,” but I just can’t. It’s instilled deep within me. So what can I do to not be the best-friend/older brother/father/confidant and be someone’s boyfriend?

— Broken Heart Bob

(more…)

9-year-old Alec Greven has written a new dating guide titled “How To Talk To Girls.” Take it from me, though, it is much easier to charm the ladies when you are an adorable 9-year-old. (I’m just bitter because a fourth-grader has more game than me!)

In a rugrats-to-riches story sure to cool the heart of every writer on this blog, Greven’s guide started as a $3 pamphlet, which was a hit at his school’s book fair, and ended up at HarperCollins, which released it to an innocence-starved nation last week.

But how’s the advice? Pretty solid. The New York Post relates:

“Pretty girls are like cars that need a lot of oil.”

He advises, “The best choice for most boys is a regular girl. Remember, some pretty girls are coldhearted when it comes to boys. Don’t let them get to you.”

True. And this Breakup Girl-esque pearl:

the best way to approach a girl is to keep it to a simple “hi.”

A 9-year-old writing about relationships just underscores what Lynn has always told me: Most dating advice is common sense; It’s just that the advice-seekers can’t access that part of their brain in their hormone-addled / douchebag-laden / games-weary / heart-flattened / rejection-paralyzed state and need to hear it from someone else. Here’s something Greven wrote that I think Lynn told me once, word-for-word: “comb your hair and don’t wear sweats.”

So where does this precocious kid go from here? He’s now writing a children’s book about Watergate! Hmmm. Take it from me, Alec, that won’t impress the ladies.

For more, check out BuzzFeed.