Sunday, November 20, 2011

Sex with Sherri or Sarah?

Okay, Grey people, I need your advice (again!) This is the grayest of grey dilemmas. For this, we’re basically going to take it back to high school, because, as much as I love my friend, she’s young, and that’s about at the level where she and all parties involved are. Should your first time be with someone you are in love with but possibly can never really be with, or with someone you’re not in love with, but who really wants to be with you? Yes, those are the only two choices.

I’m asking because I have a friend who I think is about to make a big mistake. Let’s call her Dani. Dani is in love with her best friend, Sherri. Sherri is a closeted lesbian who is engaged to be married to a boy (I say “boy” because everyone involved in this situation is 20 years old! WTF, right? Engaged at 20? But that’s another story...) How do I know that Sherri is a lesbian? Because she has been licking Dani’s vagina off and on for the past 2 years (while dating that boy, yes)! Here’s the kicker: Dani has never returned the favor! Dani is young and afraid, and struggling with her sexuality too, particularly in the wake of Sherri’s engagement to a boy. (It’s pretty clear to me that Dani and Sherri are in love, but that Sherri is simply too afraid to come to terms with her sexuality to admit this, and so maintains a farcical relationship with this poor boy.)

The dilemma comes in when Dani decides that she finally wants to have sex with a woman, and be an active participant. Dani tells me that she’s going to sleep with a friend of hers, Sarah. Sarah is, for all intents and purposes, straight, but has a thing for Dani. Dani likes Sarah, but isn’t attracted to her or in love with her. I ask Dani why she doesn’t just have sex with Sherri, seeing as though a) she’s attracted to Sherri, and b) she’s in love with Sherri. Dani says that it would be too hard to sleep with Sherri, because it would make her love for her more painful. I say that it’s better for your first time to be with someone you know well, love, and trust, than with someone you aren’t even attracted to and aren’t interested in being with.

What do you think, grey girls, boys, and zhes? Look WAY back to your first time, and pull out some pearls of wisdom!

Sorry for the simple high-school lingo, but sometimes a girl has to go there!

Peace and Love and Bugs Named Doug,


  1. Whoa! Damn! Heavy stuff for a Sunday afternoon.

    Should your first time be with someone you are in love with but possibly can never really be with...

    In this instance, I think it might not be a bad idea. It may even be the very thing that will help Sherri understand who she is, and who she can be. The emotions that surround this aspect of human sexuality are powerful and can either unite people or tear them apart. Considering that these baby girls clearly have a connection, I think they should explore it now instead of dragging it out and hurting others later.

    ...or with someone you’re not in love with, but who really wants to be with you?

    Don't play with others' emotions. If you know there's no there there, then don't mess with someone else's heart. What goes around comes around, and in situations like this, you best believe Karma's a bitch with steel-toed boots. Dani needs to keep her friendship with Sarah just that: friends. Besides, a "thing" doesn't necessarily mean anything; it could be infatuation or indigestion. Either way, it's whimsical.

    Just my $.02.

  2. Thanks, Amaya. I completely agree :-)

  3. They say that it's better the devil you know than the one you don't! I assume that by "can never really be with" you mean in a committed relationship? I'd stick with the one where feelings are known; why she'd go after a straight girl is a mystery, unless she knew for a fact this "thing" she has for Dani is going to lead to sex.

    To the last part of this, if this is about the sex, well, what's love got to do with it? Straight up, while it's "best" to have those deeper feeling for someone when sex is in the mix, they're not always necessary: You just gotta want to have the sex but there's always the possibility that "love" could follow because sometimes, love happens later and not always at the beginning.

  4. Can I vote neither?!

  5. It's funny you should say that, hotfemmeinthecity, because that's exactly what happened in the end! She has decided to wait, which I certainly can't fault her for.

    And thanks for the wisdom, KDaddy--it was imparted to the necessary party :)