Would It Be Weird For Me To Make a Move?
Q
This is gonna sound like a rom-com setup but it’s my actual life: I think I might be developing feelings for my ex-boyfriend’s sister? I dated her brother ending about six years ago for a solid three years, so I know their parents fairly well. She was away at school out of state for most of that time, so I didn’t get to know her very much back then, but what little I saw, I remember thinking she was cute and feeling intrigued by her bisexuality around the same time I was starting to realize I liked girls too. Not saying she’s my “root”…. But not saying she isn’t. Her brother is married now and lives close enough to visit but far enough away that he’s not constantly around. Now, her and I work at the same place, and I have been getting to know her, and I do think there’s something there. So, the big question is: should I let myself have feelings for the sister or is it totally out of pocket to pursue something with her?
A:
Riese: Is it super super weird? Absolutely. Is it prohibited? I don’t think so? I went ahead and googled “fell in love with ex-boyfriend’s sister” and I was like, wow this is a common query, but it turned out all those results were men who’d fallen in love with their ex-girlfriend’s sister, which does seem worse? Is this because I just saw “The Better Sister”? Probably there’s something gender rigid/essentialist about feeling that it’s worse, like that somehow two sisters are variations on a theme but a brother and a sister are different entities? Or that there are 6,000 times more straight women out there than there are queer women so for straight men it seems like ok dude just pick someone else for chrissake? IDK, maybe someone else will have insight into that. It’s just truly so hard to envision like hanging out with the same family but while dating a different sibling?? But it looks like there are other people who’ve done this and lived to tell the tale and sometimes it’s not weird.
I do think the more important factors here are that it was six years ago that you dated and that he’s married — also I’m not sure anybody’s ages here, if you dated him while you were in high school, for example, maybe it’s not as weird. But honestly I think the person most at risk for discomfort here is her — but I’m not sure there’s any way to broach it with her unless genuine feelings have been seen and acknowledged by you both. I truly think she has to be a once-in-a-lifetime love to overcome the potential weirdness. If she is then maybe this will be a really funny story to tell at your wedding!
Summer: It just occurred to me that I love writing AF+ Advice answers but I’m assessed autistic and therefore have a diagnosable condition that makes interpreting social cues difficult. Absolutely great.
But IMO? You’re not out-of-pocket for wanting this. The main factors I’m looking at to reach that conclusion are emotional distance from your ex, and evidence of horrible fallout. The worst distance to do this would be to fall for his sister while you’re still dating him. Not the case here. You’ve been separated by six years of time and he’s definitely moved on. The people involved might have completely different life stages and personalities at this point. So you’ve got a good emotional distance from the ex to make this doable.
And I also don’t see signs that there is emotional fallout to contend with. You didn’t mention a horrible separation from the ex. You’re interacting amicably with your new crush. You even have a reasonable connection (work) to start afresh. I don’t see an issue continuing this. I honestly think your real challenge is going to be dating within the same workplace.
Valerie: I agree that the biggest hurdle is probably going to be if SHE thinks it’s weird. Riese said if you dating her brother while you were in high school it might not be weird, but as an older sister, if she was in college at that time, and you were her brother’s high school girlfriend, she might not see you as “her age” at all, no matter what your ages are now. I am four years older than my brother, and it’s actually very funny to me how I see him and his friends as “little” still, even though we are all in our 30s. It would be a bit of a hurdle for me to consider dating someone I knew through my brother when he was in high school and I was in college, despite the fact that a four-year age difference wouldn’t give me pause in any other situation at my big age. I know it doesn’t really make sense, and maybe it’s an older sister/younger brother thing, or maybe it’s a “my brain is weird” thing, I don’t know, but that’s just something to consider if she doesn’t seem to be returning your feelings. Also, depending on how things ended and how close your ex was with his parents…consider you might be the family villain. The girl that broke their baby boy’s heart. So that’s something else to consider, if things would be awkward if you were ever brought home to re-meet the parents. That said, I’ve heard of MUCH stranger starts to relationships working out just fine, so it could definitely be more out of pocket.
Nico: You’re not…completely out of pocket. Just…if this happens, don’t ever discuss one with the other, I think, is a good rule. You might be tempted — but just don’t. I think Valerie’s question as to whether you might inadvertently be a family villain is a good one, maybe wise to do some investigating there. And finally, as everyone else has said, the most important person to check in here with is your crush. If she’s uncomfortable, it probably just won’t work. Speaking of “work” — what kind of workplace are you in, is actually a big factor here. Is it appropriate to have a workplace romance, or will you two see some scrutiny for that? If you think that you’re likely to be under a microscope at all, then you might expect the fact that you dated her brother in the past to come out, so just be careful out there!
What If I’m Too Intimidated To Sext Her
Q
I’m dating a writer and they are a REALLY good sexter which makes me REALLY intimidated. What I need is for you, the writers of Autostraddle, to give me tips or tell me that I should not feel this intimidated! Thank you.
A
Summer: Ahahahah oh goodness. Yeah okay, I’m a writer and online sex worker. So I have to be a great sexter or I’ll discredit both of my professions. I have input for you. You’re going to be okay.
For one, take heart. You and them are dating. And engaging s-e-x-u-a-l-l-y. They’re already into you. Whatever your sexting is, it’s already good enough to keep them interested. We can always look for areas of improvement, of course.
This one is overdone, but true. My best sexting comes from a place of genuine interest and arousal. Whether sexting at work or in a personal capacity, this remains true. When you start sexting, do what you can to make it a whole-body experience for you. If it’s appropriate, throw on some smut or porn. Draw the curtains. Settle into your comfy spot and give her your time and imagination. If you’re enjoying yourself, it’ll automatically show in the texts.
Don’t be afraid to fantasize about your next sex with her and not send it immediately. Play your fantasies out in your mind. Masturbate over them. Decorate them with sights, scents, and sounds well before you text. That way, when sexting time rolls around and your emotions are already running, you have a pre-made vision to draw on. Less stress about coming up with something good in the moment.
Everything else I leave to my fellow authors.
Kayla: I promise you shouldn’t be intimidated! Good writing and good sexting, I’ve found, are actually distinct skills. So your partner is a good writer and a good sexter, but I don’t think the latter is inherently because of the former. Which is all to say: Even if you’re not a writer, you can be very good at sexting. And I’ve sexted with writers who were just okay at sexting!!!!
For starters, you don’t even HAVE to use a lot of words in sexting —you can utilize photos and Live Photos. I love sexting, and I’m a writer, but I wouldn’t say I apply much of the craft of writing to my sexting. I’m indeed more of a visual sexter! And you don’t have to be a professional photographer to be good at taking nudes either. In general, I find with sexting that less is more —unless your partner is into excessive scene setting, just get to the point, leave some things up for imagination, and don’t overthink it.
Nico: Like Kayla said, sometimes, less is more. Leaving a bit of mystery gives your texting partner room to fill in the gaps. You don’t have to sext like you’re laying out a roadmap. You can think more about setting a scene, highlighting a moment, or throwing in a kind-of-forward curveball about something you want to do that will open the floor to more expansive conversation. And also — who doesn’t love a hot photo. One of the hottest sexts I’ve ever been sent was from a stone butch I dated extremely briefly: she sent me something very much like, “I was thinking about you the other night and my stomach dropped. I imagined touching you for the first time and seeing on your face that you knew you were about to be fucked right.” It’s somehow so hot without being explicit at all!! Art!! And no, this person was not a writer by trade.
Riese: Some articles for you:
Let’s Talk About Sexting: A Roundtable
8 Queer Sexting Experts On How We Digitally Do It
10 Tips For Better Lesbian Sexting
How To Write a Really Hot Sex in 5 Easy Steps
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OK, so I was the sister in LW’s scenario. In my case, we both liked each other. We discussed getting together, but it felt a little too weird and we basically talked it to death instead of doing anything.
More details: I had a secret crush on my brother’s high school girlfriend. She was my friend first she and I stayed friends after they broke up. She and I both came out as bi in college and after a lot of pining, we talked about our mutual feeling when we were early to mid 20s.
(Also, I accidentally submitted this comment in the submit your own question box, so AS team, pls ignore that!)
One more comment for LW1 – based on my own experience (see above) I don’t think it’s out of pocket for you to pursue your brother’s ex. But it may be a little weird. And you should be prepared for it to be weirder for her than for you.
But in my case, I think the real reason it felt too weird is because we would have been TERRIBLE for each other – and that had nothing to do with my brother and everything to do with us both being kind of messed up 20-somethings who needed more therapy and less drama. Plus, neither of us was really mature enough to not triangulate, although we tried to institute “don’t talk about [brother] rules.”