BFF boyfriends, backdoors, and Dear John

November 8, 2010 09:34:00 Posted at November 8, 2010 09:34:00
Lainey Posted by Lainey

Written by Sasha

Thanks to everyone for writing in your personal questions and thank you for trusting me with these private matters. They’ve been great and really interesting so keep them coming. In the meantime here are a few for the week…..

I hate my best friend’s bf. All of us can’t stand him. He’s so cheap and thinks he’s the man, I’m trying not to roll my eyes constantly. But she’s in love and I don’t want to piss her off but none of us want to hang out with him. My boyfriend won’t do it anymore and I just feel bad for her. Any advice? From MB


This is a really hard situation but a really easy one to answer. And it’s as simple as this: DO NOT TELL YOUR FRIEND THAT YOU HATE HER BOYFRIEND. Was that clear enough?

I say this from experience. One of my biggest regrets was openly displaying my dislike for one of my best friend’s boyfriends. At the time I thought I was just being honest and I thought she could do better. It was definitely from a place of love but she took it, and rightly so, as unsupportive. The thing is you can’t change the way someone feels--they’ve got to figure it out on their own. By speaking up, the only rift you’ll cause is the one between you and your best friend. And in the end you’ll look like the as*hole.

Do you think Will Smith’s weird scientology friends like Jada? I might be projecting but Jada Pinkett Smith is probably one of the most annoying women I’ve ever laid eyes on. Her whole ‘my sh-t don’t stink’ attitude makes me want to push her off something high. The fact remains that no matter what people say to Will, he ain’t leaving Jada for a wack load of reasons. One of them being that she’s (allegedly) his beard or he’s her beard or however that expression works.

And don’t think every girl that’s ever been with A-ROD hasn’t had a best friend begging her ass to jump f-cking ship. I’m sure Drew was all up in Cameron D’s face telling her that she was too good for him, that she was Kate Hudson’s sloppy seconds, and that she was dumpster diving in the B class. But Cameron rode that rod until she was finally good and ready to move on.

So I guess where I’m going with this is you’ve got to weigh the pros and cons. By the sounds of it, you just think your friend’s boyfriend is lame so unless he’s cheating on her, beating her, emotionally abusing her, then my advice is to zip that sh-t up tight because nothing will change until she’s ready for a change.

The only thing you should be concerned about is the relationship between you and your friend. If she’s still following good friend code, then you need to chill. However, if she starts acting weird, flaky, emotionally void, then let’s talk, because I think at that point you could bring up how you feel.

Also your friend’s not a dummy; trust me she knows how you feel. You may think you’re playing it cool but the fact that you’re ‘trying’ not to eye roll, well, I doubt you’re hiding it all that well. And FYI, if she starts to feel alienated from you and your friends, guess what? It will probably push her closer to her cheap ass boyfriend. Did you ever watch Sammi and Ronnie on Jersey Shore? I rest my case.

If your friend is happy then let her be. In the meantime just do one-on-one stuff with her for a while. I don’t know how old you are but I’m going to guess you’re still young enough that this isn’t going to be her boyfriend for forever.

You’re not always going to love everyone you meet and there will be times where you will really dislike a person that falls in your inner circle and all you can do is suck it up. So suck it up.

Hi Sasha,

Thanks so much for taking these! The back door blind item from Lainey last week got me back on a topic I wonder about and I thought you could share your opinion/insight. Movies would have us believe everybody has sex that way, and nothing makes me crazier than to see a love scene where a woman is flipped back and forth. All I can think about (and Lainey would agree, I think) is "Bacteria in the lady business!" I've been off the dating scene for a while, and back door is not something I have any interest in doing, due to that, and let's call it a "delicate stomach." But to my point, is back door the new "normal" for sex in the real world, too? Do men now expect women to agree to that right out of the gate? Is that something a woman needs to establish fairly quickly she's not going to do?

Thanks! Heidi

Damn Heidi, what movies are you watching?! …I think that sh-t is called, um, porn.

But yes, I guess you’re right, there’s a lot more in your face sex scenes and I’ll take your word for it that ass sex in film is where it’s at these days. The reason I don’t pay attention is because whenever I see a sex scene in a movie, no matter who I’m with, I get morphed back to age 12 watching Fast Times at Ridgemont High with my mom. My first reaction is to always block those scenes out- I’ll work on that one day in therapy.

Let’s get real though. This position ain’t so easy breezy. I was at a dinner party two weeks ago when this topic came up. When you’re with your best gay friends, this is a fun one to talk about. And if anyone knows the trick to this trade, it’s them, and the bottom line: heavy prep is required. My really good friend D told me that if he had a vagina there would be no way he’d be doing it from the back. Of course that’s just his opinion but I guess what I’m saying here is that this position isn’t a given. Just because they come knockin’ at the back door, doesn’t mean you have to open.

Now before I go further, let me be very clear. If you’re a woman that likes to take it up the hoop--more power to you. Congratulations. Whatever gets your rocks off. I think that’s great. High fives all around.

But Heidi, I think you and I are cut from the same ass cloth. It’s just not something I’m interested in doing. And I don’t think that makes me a prude, it just makes me someone who wants to protect my ass from penetration. That’s fair, right?

Something however that does concern me is that I think that in this day and age there are a lot of men out there who have a really tweaked idea of what girls want or are willing to do. So you need to be upfront about what you like and what you don’t. Do I think you should blurt it out on your first date? No. But if your relationship with a guy lands you in the sack and he tries to flip you around and he’s going for the money spot, then I think it’s absolutely cool to decline. It’s really as simple as that. It just means you two aren’t sexually compatible in that department. And some would argue that ‘parking in the back’ is just like a BJ. Ie. You do it for your partner even though you don’t love doing it. I don’t agree with this reasoning and I have nothing but my opinion to back this up. Either way, if it’s not what gets you off then don’t feel pressured to do it.

So Heidi, somehow the phrase PASS ON ASS seems to be appropriate in this department too. Seriously people, I’m going to start making t-shirts. Put in your order.


I met a guy shortly after my birthday, and we had an instant connection… but I wasn't ready to date, and he wasn't looking for a relationship because he was being posted to (location omitted by Lainey – just know he’s a soldier). Flash forward to today, he has been in X for nearly (a year). Lainey, knowing that you and Jacek fight and love each other every day gave my cynical little heart a little bit of hope that maybe when Lee comes home from X we can finally give things a shot.

I can't believe how fast time has gone by. In any case, we are now a mere 30 days away from him being back home...

I have been waiting for him to come for 8 months, and I am starting to realize that I made a subconscious decision of not really actively dating since he left... I am very emotionally attached to him and I care a lot about him, and honestly all I want is for him to come home safely… And then, on Halloween, I decided to pull an all-class move and hook up with a guy. Turns out he is super charming, bought me a steak dinner tonight and kissed me goodnight.

I am having such a tough time dealing with the prospect of dating someone, let alone starting to date someone (i know I'm jumping the gun) less than a month before he comes home. The new guy is really charming, has a GREAT job, and is very decent...Lee, Lee for whom my heart has been aching for the last 8 months.

What do i do?


This is like a scene from Dear John and if you know me, well, you know I like me some Channing Tatum romance. (eat it, I know he looks like Frankenstein and I’m okay with that).

First off I really think it’s great that you held out for 8 months. Because it doesn’t sound like you had any agreement with Lee to ‘wait’ for him so I do think it’s commendable that you did so without any prompting—you two must have had a really great connection before he left.

But I hope you’re not feeling bad about your Halloween hookup? I think it’s a lot to ask of yourself to stay faithful to someone you have no commitment to and this steak buying dinner guy seems to have caught your attention. Which thickens the plot…

So here are my initial thoughts. Before you even met Lee, you were mending a broken heart from a previous relationship. As you mentioned, you weren’t ready to start something new and then here comes a guy that you have a connection with but he’s leaving right away. As heartbreaking as that sounds, it’s a bit of a blessing.

This is how I see it. Lee was the perfect remedy to heal your heart and to buy you some time until you were ready to start dating again. You know what I mean? I’m not discounting that he couldn’t be a great boyfriend for you but I wonder if your 8 months of holding out had more to do with the safety of your heart as opposed to saving yourself for Lee.

Flash to 8 months later and you’re hooking up with some random guy. GREAT! To me this is a sign that you’re ready to get out there again.

Now I know the pressing matter for you is what you should do when Lee gets home. My advice is to see how it goes. Don’t feel pressured to make any decisions. Date both of them and see if you have any real feelings for either. I hope one of them pans out but if not I think you’re in a really good place to find a guy that treats you great!

Keep me posted, I need to know how this one ends.

Previous Article Next Article