Dear 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).

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Looking for help on November 9, 1998…

Dear Breakup Girl,

First of all, I LOVE your column and read it all the time. Your advice is really sensible and that’s why I’m writing — I’m hoping you might be able to help me with this. You see, I see the problem, but the solution is far from sight.

I’m 22, a virgin, had a total of 2 boyfriends (one Internet one I never met) and have a real problem getting boyfriends. OK — or anyone (I believe myself to be Bi — but since I’ve never been with anyone — I’m not sure if you can count that). I finished college, have my BA in English, am not completely unattractive, have terrible self-esteem and about 20 years of mental and emotional abuse from my father, whose house I am still living in until I save enough to get my own place. No — I have not gotten therapy for this yet — I can’t afford it and I OBVIOUSLY can’t get my father to pay for it. My mom won’t pay for it either — and she’s perfectly aware of why I need it too. (I do have a job that pays well, but I still can’t afford an apartment, much less anything big like therapy.)

I know I need to get out of my house and meet friends and people off the net, but the opportunities never seem to come up. It’s only recently that my brother taught me to recognize when other men are really flirting at me, and only recently that I realized that I am possibly attractive to other people. I used to believe that I just needed a boyfriend so bad just to have some love in my life. I still kind of half believe it. My sense tells me that I have to give that kind of love to myself before I can expect anyone else to give it. It’s harder than it sounds and I am trying to work on it. It’s hard when I’ve spent so many years hating myself for being lazy, slow, fat, unmotivated and all the other things my father spent years telling me that I am.

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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!

Going all the way — to Crazytown on September 28, 1998…

Dear Breakup Girl,

I am still a virgin. This is not a bad thing in my eyes, but it makes me REALLY shy when it comes to dating. I don’t want to have sex until I’m married, or at least engaged, I would even give it up when I’d been dating the guy for more than a year. What worries me, is that my virginity is getting in the way of my dating life. Which brings me to the fact that I’ve only had one boyfriend and that was only for a short month. Boys like me, as far as I can tell, but every time one tries to get me into a relationship, I hesitate, because I don’t like to kiss or makeout. Kissing disgusts me, and I’ve never made-out before, but I don’t think I’d like it. I don’t have much sex drive to tell you the truth. I was really boy crazy when I was younger and in high school, but now I’m not interested in physical stuff; I just want to enjoy the person I’m dating for who they are and how they make me feel, emotionally. I love one man, and he is the only one I would even think about having sex with, but he currently has a girlfriend of 1 year, and is my best guy friend in the world.

ANYWAY, back to my virginity. Is there something wrong with me, if I don’t want to hop in the sack? I’m guessing not, but it seems like the whole world is just going at it like rabbits. Another thing is that I want my husband to be either a virgin, also, or pretty darn close to one. Most guys I meet up with have a pretty large past file, or one I consider too large, and I’m turned off, even to their personality and good sides. And it’s not even like I’m going to sleep with them anyway, so I could at least date them…But the big thing is–I don’t want to be PRESSURED, and I don’t want them to try to pretend that they’ll be patient.

One of my best friends recommended that I ask my best guy friend in the whole world (yes, the one who has a steady girlfriend), to have sex with me so I know whether or not I like it, so I know if it really is something I want to save for marriage or want to experience more sooner. (more…)

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 hears from a Really Late Bloomer, who is only starting to date now at the age of 55 …

I also have never had a girlfriend and have been on only one date in my life. Part of the reason why is because from my teens up to almost age 30, I was very shy around women. As you can imagine, when I thought of asking a girl on a date, I froze with fear. I did overcome my shyness, but by then, I had settled into a lifestyle that I was very comfortable with.

Should he finish filling out his online dating profile, or is it just too late to him? Read the full letter at Happen Magazine, along with Lynn’s wise advice, then come back here and tell us what you think below!

Getting involved on March 30, 1998…

Dear Breakup Girl,

Here’s my situation. One of my friends is seeing this guy who I think is a really big jerk. In fact, I think he is extremely manipulative and emotionally abusive. Here’s a little sampling of his behavior: He constantly accuses her of having affairs with other people, even when he must know it isn’t true. He is always grilling her about her activities, trying to insinuate that she is doing something wrong — meanwhile, he can do anything he wants, including seeing his ex-girlfriend for a few drinks if he wants to. He insults her about her appearance, calls her in the middle of the night to check on her, tells her all of her friends are stupid and unworthy of hanging out with him, etc., etc. He has also had temper tantrums where he has thrown things at her, ripped up her photographs … you get the idea. I know that this is classic abusive behavior, and that the next step could be physical violence. I don’t know if it is going to go that far.

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Secrets revealed on February 2, 1998…

Dear Breakup Girl,

I’m seeing a girl who has very sensitive feelings — something I did not know about at the outset of the ‘relationship.’ It seemed that we were just seeing each other for the sake of not being lonely; there was no true love behind it. She was a virgin and I figured she was looking to change that with someone she felt close to. After we made love, she became very attracted to me, but she has told me twice that she’s not in love with me. However, she seems latched on to me and awaits every one of my phone calls obsessively.

I must admit it was a selfish thing for me to do but I need your help. I want to tell her that it’s best that we don’t see each other but I don’t know how because I know that she’ll break down and cry (she’s done it before). Basically, I don’t want to break her heart because her family and friends consider me a good person and I don’t want to change that! I want to do something now, before this situation becomes a mess! Thanks for your help.

— Danny

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