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Lesbianing with AE! This week you asked about regretful breakups and sleeping with your straight best friend

Today on Lesbianing with AE! writer Lindsey Danis tackles essential lesbian relationship problems: next steps after breakups you regret and a drunken hookup with your best friend.

Last night I slept with my best friend. We’ve known each other for the last five years (we’re both 25) and done everything together, but she has always identified as straight. I’m sure you can guess it but I was always the shoulder to cry on when some guy dumped her and the plus-one when she was single and needed someone to take to work events. She’s flirted with me when drunk, and I’ve tried hard not to read anything into it but honestly I’ve enjoyed the attention. I’ve always been crazy attracted to her, but put it out of my mind as something that could never be since she was straight. Well finally, as we were having a bottle of wine after her latest boyfriend dumped her she said she wished she could be with women because she was done with guys. I gave her a long hug, then a back massage, then things just sort of escalated. She actually took the lead. The sex we had was sweet, intimate, and amazing. It felt so different from the other women I’ve slept with. Now I’m scared and I don’t know what to do. I worry she will tell me it was all a mistake, or blame it on the drinking. I also worry she will want to give dating a try and in the process we will wreck our friendship. I texted her when I woke up that I had fun last night and I haven’t heard anything back yet so I’m kind of freaking out. What should I do?

– Forbidden Love

Hey Forbidden Love,

Being intimate with anyone involves taking a risk and being vulnerable. It’s totally normal for that to feel scary, especially if you’re the type of person to second guess everything or read a lot into a little gesture, like her not texting you back within a few hours.

Would you rather relegate this experience to the let’s-pretend-it-never-happened dustbin, or risk letting something real develop? Forget for a second about what your friend wants. What do you want? Are you willing to date your friend, a previously-identified straight girl? Are you willing to step back into the closet for a bit while she goes through a quarter-life coming out process that rewrites her truth? And are you willing to move forward if things implode, and your friendship suffers as a result?

  • Be honest with yourself, your friends and with her – If you made mistakes, own them. If you’ve changed, don’t go around telling everyone how you changed, show them. If you want to get her back and you effed things up, show that you’re not that person any more. As they say in storytelling class, SHOW DON’T TELL. Because no one wants to hear the same apology ten times, it makes things awkward.
  • Give it your best shot – Be your most charming, romantic, persuasive you and pour out your feelings.
  • Be prepared to fail – Yes, you might fail. But by not giving it a try, you will definitely fail. Your twenties are for saying “fuck it” and diving in. Taking risks. If you do not spend your twenties having grand dreams and trying to make them come true, your thirties will be an island of regrets and you’ll have one hell of a midlife crisis. (I wouldn’t know about that because I am a say yes to your dreams kind of queer lady, but I can tell you the burns of failure made really good stories. As they say, comedy=tragedy+time.)
  • Quit what’s no longer working – Aka your so-called friends.
  • Move on – Don’t make the mistake of staying hung up on this woman forever. If you try to get her back and she turns you down, move on. Trust that you will find love again — and if it’s meant to be with her, you’ll find your way back together. In the meantime, be open to new opportunities (I spent a long of time hung up on “the one that got away” and it’s no life to live.)

If she doesn’t take you back, you’ve still gotten a great gift out of this: Life Experience! For real, though: You learned a lot about yourself, worked through some bad patterns, and now you are going to be that much better of a girlfriend in your next relationship, whether it’s with the ex or someone else.

Do you have a burning question for Lindsey? Email our editor, [email protected] and write “Q for Lindsey” in the subject line, and she will get the message! No need to make it clever, just ask away!

Statistically only two percent of teenage sweethearts end up together. I know this isn’t helpful, but let it instruct you anyway. It is hopeless? Probably. Does that mean you should give up? Not until you’ve given it your all.

In all your soul-searching, have you reconsidered your so-called mutual friends? If they all took “your side” when things soured, then none of them stood up for their other good friend, your ex. None of them told you to calm down and not throw away the last five years because you were pissed off. None of them played devil’s advocate and challenged your version of the story. I don’t think those friends will serve you well going forward and I’d encourage you to find friends who can support your goals and dreams while appreciating you for you — you know, flaws and all.

What I got for you is:

  • Be honest with yourself, your friends and with her – If you made mistakes, own them. If you’ve changed, don’t go around telling everyone how you changed, show them. If you want to get her back and you effed things up, show that you’re not that person any more. As they say in storytelling class, SHOW DON’T TELL. Because no one wants to hear the same apology ten times, it makes things awkward.
  • Give it your best shot – Be your most charming, romantic, persuasive you and pour out your feelings.
  • Be prepared to fail – Yes, you might fail. But by not giving it a try, you will definitely fail. Your twenties are for saying “fuck it” and diving in. Taking risks. If you do not spend your twenties having grand dreams and trying to make them come true, your thirties will be an island of regrets and you’ll have one hell of a midlife crisis. (I wouldn’t know about that because I am a say yes to your dreams kind of queer lady, but I can tell you the burns of failure made really good stories. As they say, comedy=tragedy+time.)
  • Quit what’s no longer working – Aka your so-called friends.
  • Move on – Don’t make the mistake of staying hung up on this woman forever. If you try to get her back and she turns you down, move on. Trust that you will find love again — and if it’s meant to be with her, you’ll find your way back together. In the meantime, be open to new opportunities (I spent a long of time hung up on “the one that got away” and it’s no life to live.)

If she doesn’t take you back, you’ve still gotten a great gift out of this: Life Experience! For real, though: You learned a lot about yourself, worked through some bad patterns, and now you are going to be that much better of a girlfriend in your next relationship, whether it’s with the ex or someone else.

Do you have a burning question for Lindsey? Email our editor, [email protected] and write “Q for Lindsey” in the subject line, and she will get the message! No need to make it clever, just ask away!

Forget for a second about what your friend wants. What do you want? Are you willing to date your friend, a previously-identified straight girl? Are you willing to step back into the closet for a bit while she goes through a quarter-life coming out process that rewrites her previous truth? And are you willing to move forward if things implode, and your friendship suffers as a result?

If your friendship with this woman is the most important thing, tell her that. Say, “I know we crossed a line the other night, and I don’t want our friendship to suffer.”

If you want to explore your new connection, despite the risks, then be open about your truth. Tell her how special the night you shared was, and that you’re open to exploring a relationship if that is something she wants.

It’s not unusual for straight women to say they’re done with men, and it’s not unusual for straight women to seek emotional (and sexual) intimacy from their lesbian best friends. Even if this feels new and scary for you, it’s happened to many of us.

All you can do is own your truth and communicate honestly with your friend. Then let her decide what she wants. There’s a freedom in detaching from the outcome – in doing all you can do, and realizing the bigger picture is so much more than you – and I hope you can find that.

NEXT PAGE: Feeling Hopeless

I was with my girlfriend for 5 years. We clicked unbelievably well. We liked the same things and laughed and cried together. She became part of the family and my best friend. I trusted her more than anybody. When we both finally grew up a little bit (we are both 24) job changes and circumstances caused a little bit of friction between us as our routine went through a complete change. I didn’t see her as much even though we lived together and we didn’t communicate properly so our issues got bigger and worse over the course of a few months. I did the silly thing and spoke to our mutual friends, who seemed to be siding with my opinion. I didn’t really see this at the time. After an argument on a birthday night out, my friends sort of turned against her. I know this is partially my fault for telling them most of the bad rather than the good. Long story short 3 months later I’m breaking up with her on New Year’s Day because opinions have me convinced we are just not right for each other.

I knew I made a mistake letting this girl go, and in the last 6 months I have grown up massively because of it. All of the issues I had I have worked endlessly on. I really took the time to try and make myself a better person, trying not to punish myself more. Despite this, I’m scared it’s too late to fix my mess. My ex is the most stubborn person in the world and is convinced we can’t fix our issues and that we can’t rebuild the trust we once had. Is there still hope? Or am I holding on to nothing? Is life just telling me this isn’t right anymore? I know now more than ever that this is the person I am meant to be with.

-Hopeless

Hopeless,

I’m kind of a romantic, so I want to tell you to go for this. To write her a letter, do the romantic gesture, pour your heart out.

But I’m more stubborn than sweet, so when I’ve crossed someone off my list there is a 0.00001 chance of me coming around. If your ex is like me, then things are probably hopeless (though you never know unless you try).

So. You’re gonna give this your best shot. And it might fail.

Hell, you might’ve already given this your best shot. You’ve tried to tell the ex how much you miss her and that you regret ending things, but she is unwilling to let you back in. I don’t know if you two can rebuild trust, since I don’t know who did what (readers, take note: If you write in and you want me to give you the best possible lesbian dating advice, don’t skimp on the details!) But you have to be willing to give it a try, and it sounds like she isn’t.

You two got together when you were 19 and you shared pivotal years. I bet you enjoyed crazy adventures, shared your hopes and dreams, and built something incredible together. But it didn’t last. Your priorities shifted (or hers — from your letter I’m really not sure what happened) and you weren’t able to continue to grow together, and here you are heartbroken.

Statistically only two percent of teenage sweethearts end up together. It’s incredibly rare for a love connection formed so young to last decades, especially during the sea change of your twenties when your priorities and goals are changing rapidly. I know this isn’t helpful, but let it instruct you anyway. It is hopeless? Probably. Does that mean you should give up? Not until you’ve given it your all.

Statistically only two percent of teenage sweethearts end up together. I know this isn’t helpful, but let it instruct you anyway. It is hopeless? Probably. Does that mean you should give up? Not until you’ve given it your all.

In all your soul-searching, have you reconsidered your so-called mutual friends? If they all took “your side” when things soured, then none of them stood up for their other good friend, your ex. None of them told you to calm down and not throw away the last five years because you were pissed off. None of them played devil’s advocate and challenged your version of the story. I don’t think those friends will serve you well going forward and I’d encourage you to find friends who can support your goals and dreams while appreciating you for you — you know, flaws and all.

What I got for you is:

  • Be honest with yourself, your friends and with her – If you made mistakes, own them. If you’ve changed, don’t go around telling everyone how you changed, show them. If you want to get her back and you effed things up, show that you’re not that person any more. As they say in storytelling class, SHOW DON’T TELL. Because no one wants to hear the same apology ten times, it makes things awkward.
  • Give it your best shot – Be your most charming, romantic, persuasive you and pour out your feelings.
  • Be prepared to fail – Yes, you might fail. But by not giving it a try, you will definitely fail. Your twenties are for saying “fuck it” and diving in. Taking risks. If you do not spend your twenties having grand dreams and trying to make them come true, your thirties will be an island of regrets and you’ll have one hell of a midlife crisis. (I wouldn’t know about that because I am a say yes to your dreams kind of queer lady, but I can tell you the burns of failure made really good stories. As they say, comedy=tragedy+time.)
  • Quit what’s no longer working – Aka your so-called friends.
  • Move on – Don’t make the mistake of staying hung up on this woman forever. If you try to get her back and she turns you down, move on. Trust that you will find love again — and if it’s meant to be with her, you’ll find your way back together. In the meantime, be open to new opportunities (I spent a long of time hung up on “the one that got away” and it’s no life to live.)

If she doesn’t take you back, you’ve still gotten a great gift out of this: Life Experience! For real, though: You learned a lot about yourself, worked through some bad patterns, and now you are going to be that much better of a girlfriend in your next relationship, whether it’s with the ex or someone else.

Do you have a burning question for Lindsey? Email our editor, [email protected] and write “Q for Lindsey” in the subject line, and she will get the message! No need to make it clever, just ask away!

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