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February 28

The Night Visitor

Filed under: Advice — posted by Breakup Girl @ 9:30 am

Ghosts of boyfriends past visiting on December 7, 1998

Dear Breakup Girl,

I feel as though I’m experiencing a sitcom “inner dialogue/fantasy sequence”…it’s so cliche as to be deeply disturbing. I’ve been broken up since February and just recently started dating again…er, and venturing into nakedness with other men…

The problem is I keep thinking of my ex during all “intimate” activities. It’s so distracting that can’t enjoy myself and I feel terribly impolite (even though the guy I’m with has no idea). This has really never happened before. How can I make this ghostly bedfellow disappear??

— Clare

Dear Clare,

I’ve said it before, I’ll say it again: when you sleep with someone, you sleep with everyone else you’ve slept with.

I mean, you can toss their stuff off the balcony, but the muscle-memory of sex and intimacy will stay much more firmly lodged under your skin. Which means that to some degree — when you get naked with someone new — that ghostly presence in your pores is normal. And thus that to some degree, letting him be — rather than distracting yourself by trying to shove him from your mind — is what will help fade him out.

Also, make sure you actually like these naked boys. ‘Cause that ghost guy might also be Banquo. Wondering: “What are you thinking!?”

Breakup Girl


February 27

Does size matter?

Filed under: Advice — posted by Breakup Girl @ 9:36 am

Measuring up on December 7, 1998

Dear Breakup Girl,

I am a 17 year-old male. Please please please let me know what you think about penis size. Does size matter? You can laugh at me, make jokes, anything, but please let us know your thoughts on this. Please.

— Shain

Dear Shain,

Breakup Mom, didn’t you leave something on the stove?

Still, I’m going to play it safe and quote someone else on this one. In this month’s issue of P.O.V., Sheri De Borchgrave writes: “Yes, size does matter. Now get over it. Most guys are just right, i.e. average. They measure in at a proud five or six inches with a 1.25 inch diameter. But remember, a poorly handled weapon [note: BG does not endorse this word choice] of any size is useless. Size does matter, but so does good technique… Your mission: go forth and find the right fit, and stop obsessing about the size of your manhood. Men have hatched this absurd collective paranoia. Remember: in the end, what [women, or whomever your partners] really care about is not how big you are, but how big your desire is to satisfy us.”

BG’s finesse: it’s not that your partner will be unsatisfied if you are small (“small”). It’s that your partner will be unsatisfied if you act small.

This is information you will use when you are ready, in like, four years, right, Shain?

Breakup Girl


November 12

True Confessions: She bared her skin … but not her heart!

Filed under: Advice — posted by Breakup Girl @ 10:24 am

truecircleDear Breakup Girl,

I’ve never seen such good relationship advice on a website. You rule, therefore maybe you can help me. Six months ago I met AMY, a girl who I had intense *POW* chemistry with. I mean it, when we first made eye contact it was like my tongue hit an electric socket. She felt it too, I found out later. Not because either of us is extremely attractive, you understand, it was just “there” you know?

Anyhoo, I am 26, a few girlfriends and one live-in experience that lasted a year. Amy, however, was (and likely still is) a virgin at age 27. She told me right up front that she was conservative, didn’t like public displays of affection, didn’t often date, and had never been in a relationship longer than 3 weeks. I thought this was odd, but accepted it. She also told me after knowing me two weeks that she was NOT EVER going to sleep with me. This stunned me, because I usually don’t go into relationships deciding whether or not I’m going to DO something — I usually just let it happen. This hurt my feelings when she said it, but after we talked about it we decided to keep dating. This was probably my first mistake, but keep reading.

To contradict all Amy told me about herself, our dating pattern didn’t seem to fit. We would commonly meet for lunch, which would turn into a long talk, then a matinee, followed by dinner, followed by searing makeout sessions that would leave my lips bruised the next day. These dates happened once or twice a week, and ended at 2 AM when she (or I) would pry ourselves away (no sleepovers, no intercourse allowed) and drive home. The dates always lasted many hours, and even after spending almost 10 or 12 hours together, she would say “I wish I could spend more time with you etc.” By our third or 4th date she had gone from not wanting to hug me in public to kissing me (with tongue) while we were at a table in a restaurant (in a secluded booth, and I didn’t object).



October 1

This week at Happen: He’s not affectionate — at all!

Filed under: Advice — posted by Breakup Girl @ 9:42 am

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 atHappen now as well.

This week Lynn aids a girl who feels Untouchable. She recently met a boy through Internet dating, but is having a hard time making a physical connection:

I am a very affectionate person; I am always touching his back or playing with his hair, that sort of thing. He seems to appreciate it… but he shows no affection back. We have become intimate recently, and he always has his eyes closed.

Can this be worked on? If so, how should she approach the subject? Read the full letter at Happen, then add your own two cents in the comments below.


August 27

How do I have sex with him without hurting his feelings?

Filed under: Advice — posted by Breakup Girl @ 9:35 am

Feels like the first time on November 2, 1998

Dear Breakup Girl,

Ok, I hate asking for advice. About anything. I detest asking for directions when I’m driving (I get lost a lot) and I really, really, really hate asking advice about anything personal. But, jeez, I’m confused. No, wait, nervous is more like it. Here’s the deal: I have a boyfriend. I love him a lot. We have a good relationship. He’s totally sweet, I’ve known him since I was a freshman (I’m 18 now and in college) and he was a sophomore in high school. In fact, we once dated [three years ago] too. So our relationship has a pretty strong base. I’m completely secure and happy. Great. Super. Wonderful. Right? Problem is, we recently agreed to start having sex. Now this is not a “should we or shouldn’t we” are we ready kind of question. I know I’m ready. I’m not a virgin, haven’t been for a while, and I’m comfortable with that. It’s not like I’ve been sleeping around. I lost my virginity two and a half years ago to my best friend…it was a mutual curiosity thing, and I’m glad I lost it to someone I love as much as him…even in a friendly way. I’ve been with two other guys since (both long-term relationships) and haven’t felt guilty or weird at all. Until now. Cuz, see, the thing is, well, he (my boyfriend) is a virgin. Yep, 19 years old, never slept with anybody. Don’t get me wrong, I love that. I think it’s totally cute. It makes him even more attractive. I just feel kinda strange having quite a bit more experience than him. He knows he won’t be my first, we have an honest relationship. And I can tell it’s weird for him. I know he still really cares for me and all, but I think it’s like, painful for him to think about other me with other guys. In fact, he told me so. How do I put him at ease? I love the guy, and I feel so loved and flattered that he would sleep with me. I know he’s turned down lots of other girls, so for him to feel ready to sleep with me, only me, really says a lot for his feelings. He’s a really sensitive guy (almost scarily femininely sensitive) and I want him to know that it is equally special for me, which it is. So it basically boils down to this: How do I have sex with him without hurting his feelings? Strange question, I know, but I’m worried! Thanks a bunch…

— Nicole

BG’s answer after the jump!


August 8

I want more talking and less sex

Filed under: Advice — posted by Breakup Girl @ 7:56 am

fantasyTalking is overrated on November 2, 1998

Dear Breakup Girl,

A year ago I walked into the first day of class and saw the most beautiful girl I had seen in a VERY long time. I had a huge crush instantly. Everyone has certain criteria, whether they know them or not, and She meets all of mine. Intelligent, funny, caring, active, silly, an incredible smile, beautiful eyes… ouch!

Anyways, a few months later I noticed her talking to me more frequently and had the feeling something was happening but thought nothing of it. While we were in Toronto for a conference, we went out with mutual friends one night. Her friend, whom she was staying with suggested I crash at her place since it was closer. I’m thinking, “great idea, She’s staying there!” Anyways, the friend, the crush, and I went back to the friend’s place, and we stayed up talking for a while, then went to our respective rooms. 45 minutes later I’m woken up by my door opening and She’s crawling into my bed saying she was cold. I’m thinking “I will keep my hands to myself,” but that quickly changed when she started kissing the back of my neck. Anyways, skipping ahead two hours,we both agreed that we were not looking for a relationship since our course/work-load simply didn’t leave enough time for one. After getting back to school, we found that the course-load did not decrease our sex drives.

We both found that while we had trouble keeping our hands off each other, the most important part of a relationship, communication, was going nowhere. Auuugh!!! It would seem like we’d just run out of things to say. I don’t think there was anything worse than feeling like I didn’t have anything to talk to her about. I even started to plan ahead what I could talk to her about at one point! Anyways, we broke up after about one and a half months because we agreed that we were missing something pretty and important; communication.



June 15

Keeping the lights on

Filed under: Advice — posted by Breakup Girl @ 8:13 am

Fooling around on October 19, 1998

Dear Breakup Girl,

What’s a good way to tell my sweet, incredible boyfriend that I think he’s beautiful and I adore his body, even though he’s fat, and I’d like the lights on once in a while (nudge nudge, wink wink)?

— In the Dark

Dear Dark,

You pretty much already know, but I’m so glad you asked. How about saying, “Sweet incredible boyfriend, I think you’re beautiful and I adore your body. I love what we do in the dark, but I’d also love to try having the lights on once in a while.What do you think?” If he’s bashful, start with lots of candles (think: that scene in the new “Romeo + Juliet,” except without the death part). Alternatively, you could simply “show, not tell” (nudge nudge wink wink).

See, shy big/beautiful people out there? Saying, confidently, “Here I am!” — as opposed to hiding — is what’s truly hottest of all.

Breakup Girl


May 2

Confused yet satisfied

Filed under: Advice — posted by Breakup Girl @ 8:49 am

Sex with an Ex on October 12, 1998

Dear Breakup Girl,

Let’s-call-him-Jack and I have been broken up for nearly six months after dating for nearly 3 years. We tried the friend thing for a while and it worked out quite nicely except I foolishly took every nicety as a sign that he wanted me back. But now I know that just isn’t going to happen and I’m fine with it, although I still think about him every day, multiple times a day. However, I sort of have the hots for someone else AND am enjoying being single. My question is, Jack and I started sleeping together again in late June (we broke up in March) and have done it 5 times since then. We are always drunk when this happens but the sex is INCREDIBLE. The first few times he would not kiss me and we would not cuddle afterwards, just roll over and go to sleep. However, I mentioned the no-kissing policy made me feel like a prostitute so the last two times he has kissed me and held me BEFORE and AFTER we did it. The problem is, I know it is stupid to have sex with an ex, but what if it is REALLY good and you aren’t nursing false hopes of reconciliation? Also, what’s up with the kissing thing? Please help!!!

— Confused yet Satisfied

Dear Confused yet Satisfied,

I’ve said it before, I’ll say it again: of course the sex rocks your world. There’s no aphrodisiac like a breakup. As in, “You look great without … commitment.”



March 2

Should I be committed?

Filed under: Advice — posted by Breakup Girl @ 9:13 am

Crazy about men on September 21, 1998

Dear Breakup Girl,

Ok, so here’s the deal. I love sex, I love men and I love life. What I don’t want is a committment. I don’t want a boyfriend. My roommate says this makes me dysfunctional and self-destructive. She disapproves of my (safe) one-nighters or casual sex relationships. I say it is perfectly healthy … the reason I don’t want to have a relationship with anyone is because I have not yet met the man who deserves me. I am a great girl — smart, funny, generous, pretty (ok, I’ll stop, sorry) — and confident. I need a man who can handle all that and live up to some pretty high standards. Relationships, as you well know, take time and effort and a great deal of respect, trust and committment. Why should I give all those very precious things to someone unworthy? So what I’m saying is that I am 20 and I have a lot of life to live — so there’s nothing wrong with filling that life with beautiful men who make me happy, if only for a night (no — I don’t have any feelings of unfulfillment), lovely poetry and moonlit nights? What do you think? Am I delusional? Am I ok? Am I heading for a very large mid-life crisis and an exorbitant therapy bill?

— Siobhan

Dear Siobhan,

No, you’re fine. So are standards. Just make sure of one thing: when he comes along, will you actually let him in?

Breakup Girl


February 22

Giving up on “giving it up”

Filed under: Advice — posted by Breakup Girl @ 8:53 am

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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