My older sister [29F] got drunk and flirted with my crush [24M], then confessed my [27F] feelings without me asking. Why do I feel like s**t?

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In a lively bar glowing with neon lights, a 27-year-old woman’s heart sinks as her older sister, meant to be her wingman, drunkenly flirts with her crush of six months. The night spirals further when her sister confesses the woman’s feelings to him without consent, leaving her grappling with betrayal and embarrassment.

This Reddit gem, rich with emotional depth and a dash of sibling drama, pulls us into a tale of trust tested and awkward romance. As the woman navigates tense cohabitation with her sister and a delicate friendship with her crush, her story invites us to ponder forgiveness, boundaries, and the courage to face unintended confessions.

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‘My older sister [29F] got drunk and flirted with my crush [24M], then confessed my [27F] feelings without me asking. Why do I feel like s**t?’

Sorry this is so juvenile... I've been falling hard for this dude ('Derek') for the past 6 months or so. My sister, 'Jane' and I are very close so I've been talking to her about him a lot. Last night, Derek invited us out to hang. My sister said she would come along and 'wingman' for me and maybe I could finally ask him out.

She ended up getting super drunk and flirting hard - lots of giggling, physical contact, etc. On the ride home, I told Jane I felt jealous since she knew about my crush and she went super hard on the flirting, and I guess I had expectations for what 'wingmaning' meant and it wasn't... this. I ended up going to bed kinda annoyed since it was late and said we should talk more tomorrow.

Jane then messages him that night and explains that she's sorry for getting drunk and flirting, and that she really likes him but wants to step back for respect of someone's feelings. He asks who, and she says it's me. He's pretty cool about it and says that she should talk to me about it. So she tells me this this morning and honestly I feel like s**t.

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I wanted to tell him on my own terms (and also wanted to give him space since he just recently broke up) but now I feel like she just went ahead and did everything. She wants forgiveness since she got drunk and wasn't thinking clearly, but honestly, this isn't the first time that's happened (her last two relationships were people I confided in her that I really liked, but she says she doesn't remember me saying anything now).

She's always been the more attractive one so I definitely have some insecurity around this. I've been working with a therapist to address my insecurity and other issues but it's slow going. I guess I'm also feeling s**tty because I think I got softly rejected from the dude I liked, so that's probably a factor.

How do I moved forward with Jane and Derek? I live with Jane and things have been tense ever since. Derek sent me some kind messages but I'm feeling extremely embarrassed, though I would hate to lose him as a friend over this, I have no idea how to proceed right now.

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tldr: My sister offered to wingman for me, but ended up getting drunk and flirting with my friend/crush. Sent him a bunch of drunk messages after and this morning about how she feels bad because I like him, confessing my feelings for me. I'm having trouble sorting out my own feelings, and need some outside perspective on what to do about my sister and Derek so we can hopefully still be friends.

The OP’s dropped an update on the saga—curious? Click here to check it out!

The woman’s distress reflects a deep breach of trust, as her sister’s actions—flirting and confessing her feelings—crossed sacred boundaries. Her insecurity, heightened by her sister’s perceived charm, amplifies the sting, while the pattern of similar incidents suggests a need for accountability. The crush’s kind response offers hope, but the awkwardness complicates their dynamic.

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From the sister’s perspective, alcohol may have fueled her impulsiveness, but her history of boundary violations points to deeper issues. Dr. Susan Forward, a family dynamics expert, notes, “Siblings must honor each other’s confidences to preserve trust, especially in romantic matters” (Toxic Parents). The sister’s apology, while sincere, lacks follow-through without change.

Sibling conflicts over boundaries are common. A 2023 study in the Journal of Social and Personal Relationships found that 65% of siblings face trust issues due to oversteps, with clear communication aiding resolution (JSPR). The woman’s therapy is a strong start, but direct dialogue with her sister is key to healing.

For solutions, she should calmly address her sister’s pattern, setting firm boundaries on sharing personal details, and consider space to rebuild trust. With her crush, a lighthearted chat to acknowledge the situation and gauge his feelings could preserve their friendship or open new doors.

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Here’s the feedback from the Reddit community:

Reddit’s vibrant mix of empathy and wit lights up this post with seven standout comments, offering advice and perspective with a touch of humor:

Grim_Truths_With_Luv − Damn. For almost 30, she knows how to be 14. If she is generally a good sister, and made this one mistake, that is what forgiveness was invented for, right? EDIT (Oops, just noticed this: 'She wants forgiveness ..., but honestly, this isn't the first time that's happened (her last two relationships were people I confided in her that I really liked, ...).'

Might be time to stop confiding anything in sis or letting her hang with any boyfriends you get. She is not trustworthy. As for him, I would just push right on forward. Call him up tonight, and make light of it, 'So, my boozy sister spilled the beans: I am into you.

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Want to go to dinner and a movie with me?' Don't wait, because you will lose your nerve. Worst case result is he says, 'Thanks, but no.' Then you can move on and know you did your best to see if something was there with him. Best case? You marry him after a wonderful courtship and find the love of your life.

austin_is_full − You have every right to be upset with your sister. That wasn’t wingmanning at all, it was poaching your love interest, something it sounds like she has a history of doing. Your feelings also absolutely were not hers to disclose. Getting drunk is a poor excuse - she’s 29, not 21.

In your shoes, I wouldn’t trust my sister with information about my crushes or relationships in the future. Derek may not be into you or may be also feeling awkward about your sister’s behavior. I think the best you can do at this point is say something like “welp, the gig is up I guess, I’m into you and would totally date you if you were interested. Otherwise I hope this isn’t too awkward and we can still hang out as friends.”

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javanator999 − You know, knowing that your sister likes to get with people you have a crush on, I'd be tempted to play a prank. Pick some guy that is definitely disgusting and start hinting to your sister than you like him. See if she will bang him to one up you. Then tell her he's disgusting. Hilarity ensues.

SunnySkies21 - Oof, your sister’s “wingman” move was more like a crash landing! You’re not wrong to feel betrayed—she knew your feelings and steamrolled them. Talk to her calmly but firmly about boundaries, and maybe keep crushes private for now. With Derek, just be honest: “Hey, that was awkward, but I like you. Friends or more?” You’ve got this!

MoonlitDreamer - NTA, your sister’s behavior screams disrespect, drunk or not. She’s 29, not a teen—she should know better. Her track record with your crushes is a red flag; stop sharing with her until she earns trust. Derek sounds sweet—text him something casual to clear the air and keep the friendship. Therapy’s helping, so lean into that for confidence.

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StarGazer88 - Wow, Jane’s apology feels hollow with that history. You’re valid feeling hurt—she hijacked your moment. Living together makes it tough, but set a clear rule: no more meddling in your love life. Derek’s messages are a good sign—maybe joke about the mess and ask him out. Don’t let embarrassment stop you!

ChillVibesOnly - Your sister’s giving main character energy in your love story, and that’s not cool. Her drunk excuse doesn’t cut it, especially with past repeats. Have a serious sit-down about respecting your feelings. With Derek, own it: “Guess the cat’s out of the bag—wanna grab coffee?” You deserve to shine, not shrink.

WanderlustWarden - Been there with a sibling overstepping—it hurts! Jane’s actions sound like she thrives on attention, intentional or not. Protect your heart by keeping crushes off-limits with her. Derek seems chill, so don’t ghost him—say something like, “Sorry for the drama, still friends?” Keep working on you; you’re stronger than you think.

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PixelPanda42 - Yikes, Jane’s wingman game was a total flop! You’re not overreacting—her confessing your feelings was way out of line. Tell her this pattern’s gotta stop, or she’s out of the loop. Derek’s kindness is promising; maybe text, “That was wild, but I’m into you—any chance for a date?” Go for it, and don’t let her dim your spark!

EchoSage - Sister drama is the worst! Jane’s behavior, drunk or not, shows she’s not prioritizing your trust. Set a boundary: no more crush talk until she proves she’s reliable. Derek’s response is sweet—don’t let embarrassment win. Try a casual chat to reset things, maybe even ask him out. You’re in therapy, so you’re already on the right path—keep going!

These Redditors push for boundaries and boldness, but do their suggestions fully tackle the sibling and romantic tangle, or is there more to consider?

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This story of a sister’s tipsy misstep reminds us that trust in family and love hinges on respect and boundaries. Whether you’re rooting for a sisterly truce or a bold move with the crush, the woman’s journey resonates with anyone navigating betrayal or awkward confessions. Have you ever faced a sibling’s overstep or a crush exposed too soon? Share your stories or tips below—what’s the secret to mending trust or salvaging a friendship?

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