How to reply to my boss‘s flirtatious message?

I'm a 24-year-old intern at an investment bank in NYC. Last night, at a team gathering, my married male manager made me an alcoholic drink, waited with me for my Uber, and later texted me saying, 'You're really something special, you know?' He has a say in whether I get a return offer, so I don't want to upset him, but it feels off.

🤔 Am I overreacting? How should I respond?

#letschat #workplacetips #negotiationtips #conversation #Internship

2024/9/19 Edited to

... Read moreNavigating workplace dynamics can be incredibly tricky, especially when a boss crosses a line. When my manager sent that text, I immediately felt a wave of confusion and anxiety. Was he just being friendly, or was this actual flirting? Many of us wonder, 'is my boss flirting with me or just friendly?' It’s hard to tell sometimes, but trust your gut feeling if something feels 'off.' I learned that recognizing the signs is key. If compliments become overly personal, if there’s an unusual amount of private messaging, or if they seem to treat you differently than others in a way that makes you uncomfortable, those could be red flags. My manager's 'you're special' text after an alcoholic drink and waiting for my Uber definitely crossed into that ambiguous, uncomfortable territory for me. After a lot of thought, I decided to go with a mix of strategies, starting with Subtle Rejection. This isn't about being rude or confrontational but gently redirecting the conversation back to work. For instance, if he complimented my work ethic, I'd reply, "Thanks! I'm really enjoying learning from the team's expertise here." It deflects personal attention and reinforces professional boundaries. The goal is to make it clear, without explicitly saying 'don't flirt with me,' that your focus is purely professional. Another crucial step was Boundary-setting. This meant being very clear in my communication, even if indirect. If he’d tried to initiate another non-work conversation after hours, I might reply something like, "Thanks for reaching out! I'm actually wrapping up for the night, but happy to discuss X project tomorrow during work hours." This way, you're not accusing but you're subtly defining the appropriate time and context for interaction. It's about questioning the manager's behavior in a non-aggressive way by demonstrating what is appropriate. Sometimes, the best response is no response at all, which aligns with the Cold Treatment approach suggested in some advice. If the message isn't directly work-related and feels inappropriate, simply not replying can send a powerful message. It shows you're not engaging with the non-professional aspect. However, I combined this with another vital strategy: documenting all inappropriate interactions. I kept a private journal, noting down dates, times, specific messages, and what happened. This isn't just for my peace of mind; it's crucial if the situation escalates and you ever need to consider reporting to HR. Protecting your career while navigating an awkward situation like this is a delicate balance. It's about being professional, setting clear boundaries, and protecting yourself. Remember, your comfort and professional integrity are paramount. No job is worth compromising that.

29 comments

Bailey 🖤's images
Bailey 🖤

I actually like the idea of keeping a record of everything. You can NEVER be too safe. Do not be afraid to speak up, no matter the consequences.

See more(1)
Zirconlil's images
Zirconlil

You are not overreacting. It is really creepy, and I would not be surprised if he ended up escalating things definitely keep a record of this.

See more comments

Related posts

A collage featuring a woman with long dark hair and glasses, with text overlay indicating these are iMessage stickers and instructions on how to add them.
A man, possibly Snoop Dogg, is lying in bed with a head covering, looking directly at the camera with a tired expression.
A young child with curly dark hair and pink hair clips looks up and to the side, wearing a light purple top.
Part 2 stickers I have on iMessage 💬
Feel free to steal them🥲 I had to add my daughter in this one (2nd sticker)🤣🤏🏾 she’s a keekeee honey! 🤣 make sure you like and follow meeee ⭐️leave a comment I reply I’m not one of them!⭐️ #imessage stickers #randomtags #phoneforideas #roomtour #summerbod
5⭐️Brat

5⭐️Brat

1385 likes

3 more days until Fitness challenge!
#homeworkout #athomeworkout
Lovediamondly

Lovediamondly

147 likes

Replying to @BIGCEE’🧚🏽‍♂️
Jeanè Mariee

Jeanè Mariee

196 likes

The cover image for an article titled "The 3 Types of Ghosting And How Each One Ends," set against a tranquil garden pond with lush greenery and traditional structures.
Describes "The Placeholder" type of ghosting, characterized by constant but non-committal interaction, set against a cozy indoor scene with a sofa and a small dog.
Explains "The Reappearance" ghosting, where someone vanishes then casually returns without acknowledging the gap, overlaid on a dark, blurred road scene at dusk.
How to respond to ghosting
Ghosting isn’t confusing. Your response to it is. Most women don’t stay stuck because they didn’t see the pattern. They stay stuck because they kept interacting with it. 𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗵𝗮𝗽𝗽𝗲𝗻𝘀: He doesn’t choose → but he doesn’t leave He disappears → then checks if you’re stil
Cariño ♎️👸🏽

Cariño ♎️👸🏽

255 likes

A message to the mothers of the world
Nickwilkins

Nickwilkins

2055 likes

A woman with long dark hair, wearing a black jacket, with text overlay: 'REPLY TO HIM LIKE THIS High Value responses to low effort.' The Lemon8 logo and username are at the bottom.
Text on a white background titled 'The "Dry Text" Killer', detailing scenarios of low effort texts, common mistakes, and high-value scripts with psychological explanations.
Text on a white background titled 'The "Late Reply" Check', outlining scenarios of late replies, common mistakes, and high-value scripts with psychological explanations.
How to handle "Low Effort" men
(Copy & Paste Scripts). 💅🚫 Psychology Series: Part 31 📲 If you accept crumbs, you will starve. Many girls kill their own value by over-rewarding Low Effort behavior. If he texts you "WYD" at 11 PM and you reply instantly... you just told him: "I have no life and I am waiting for
Emily | Mindset & Growth

Emily | Mindset & Growth

467 likes

A woman stands in a modern space with wooden walls and plants, holding a drink. An overlay reads, "this your sign to message those brands," encouraging proactive outreach. The image promotes content creators to engage with brands for potential collaborations.
HOW I GET BRANDS TO REACH OUT TO ME ☁️✨🌷💗🎀
MESSAGE THOSE BRANDS ‼️‼️ Don’t be afraid to put yourself out there, even if they don’t reply right away! 🌟 Building connections takes time, and every message you send is a step closer to your goals. 💌 Whether you’re pitching for a collab, introducing yourself, or just expressing how much you l
Faith | UGC

Faith | UGC

118 likes

How to Half Swipe on Snapchat to Read Messages
Want to read someone’s message on Snapchat without them knowing you’ve opened it? The Half Swipe trick is a clever way to do just that — giving you a sneak peek at the chat without triggering the “Opened” status. It only works for text messages (not snaps or videos), but it’s a game-changer when yo
Lily Brown

Lily Brown

720 likes

Bigsexy81

Bigsexy81

597 likes

Why did I have a peanut costume?
#costume #nut #dastardly #commitment
Forrest Valkai

Forrest Valkai

180 likes

A screenshot of a text message from 'Daniel' saying, 'You're really something special, you know?' The image asks, 'How should I reply to my boss's flirtatious messages?' and shows a text input field.
A text message exchange where 'Daniel' says, 'You're really something special, you know?' The user replies, 'Thanks, but I have a boyfriend.' Daniel responds, 'Yeah, no worries! We were just having fun, nothing more than that, right?' Coach's feedback states the response lacks tact.
A text message exchange where 'Daniel' says, 'You're really something special, you know?' The user replies diplomatically, acknowledging the compliment and praising the team. Daniel responds, 'The team's great, yeah, but let's be real—your work stands out. Don't worry though, it's all good, just friendly vibes here.' This is labeled 'Subtle Rejection'.
My boss has a crush on me… how do I turn him down?
I'm a 24-year-old intern at an investment bank in NYC. Last night, at a team gathering, my married male manager made me an alcoholic drink, waited with me for my Uber, and later texted me saying, 'You're really something special, you know?' He has a say in whether I get a return off
ConvPro.com

ConvPro.com

3 likes

Tool to Reply any email, message, anywhere
Meet your ultimate reply shortcut: effortlessly respond to emails, messages, anytime, anywhere, with just one click! No more juggling tabs or wasting time searching for responses. This tool streamlines your communication, ensuring swift replies with minimal effort. Whether it's an email fro
Reverelia

Reverelia

28 likes

not a problem
#give #money #success
necroscratcher

necroscratcher

60 likes

‼️🚨MARY GAVE A MESSAGE FOR U 🙏💙
Take a quiet moment to reflect on these words… “My children, my glorious children… You are my heart 🩷 Bring to me today all of your questions. I will take them to my Son and bring you answers. My love for you is beyond the depths of the ocean 🌊 and my heart overflows with joy in seeing you s
Roots Rising

Roots Rising

1 like

A stylized illustration of a woman with curly hair, holding a phone. Overlay text reads "Why I don't reply to Messages on Lemon8" and "Lemon8 @openfile1988".
I don’t reply to messages on here
I have been on this app for going on two months. I downloaded this app thinking it was for females because the way Instagram advertised it. like a clean girl makeup and other things. So i downloaded it thinking I would gain female followers. I didn’t really want to post any pics because this accoun
R3Dz

R3Dz

28 likes

How to relax your nervous system before bed
Your body doesn’t just need rest It needs a signal that it’s safe Try this instead: • Close one small “open loop” Reply to one message, tidy one corner, finish one tiny task → your brain relaxes when things feel complete • Change the temperature Wash your hands with warm water or step
sychugovacandlehouse

sychugovacandlehouse

6 likes

A title card with text 'text messages from HIM that give me chills every time' overlaid on an image of two shadows walking on a path.
A screenshot of a text message from a boyfriend saying, 'Well I know for a fact that you're my soulmate,' with reaction options.
A screenshot of a text message from a boyfriend expressing how much he misses her and thinks about her constantly.
Text Message Series #2: Boyfriend
This is my first EVER relationship. I never really had a guide in first relationships and so everything i’ve been learning is on my own! What do you mean a guide in first relationships? Well, what I mean is that I’m dating someone who’s had experience in previous relationships. I have ZERO exper
djaliana herring !

djaliana herring !

1472 likes

How To Reply When Your Feelings Are Hurt 💔
Handling a text that stings can be tough, but it’s important to respond thoughtfully. Here’s a cute lil guide to help you navigate these situations. **1. Take a Breather:** Before replying, pause and take a deep breath. This helps you avoid reacting impulsively. Give yourself a moment to process
ZINNIABEA SAGED

ZINNIABEA SAGED

13 likes

Y’all trippin
bodieneme

bodieneme

46 likes

Unos ricos frijoles de La holla
#feijolesdelahollas #recetas #lemon8foodhacks
Maria 🤍

Maria 🤍

9 likes

when they don’t reply to your text 🥺
#singing #piano #acoustic #ghosted
Lindsey Jade

Lindsey Jade

28 likes

Why don’t more people know about AIP?
I have been trying to find a place to dedicate to spreading the word on what the AIP diet is & post only AIP focused content to in order to help people get this information and have to sift through less. I found the place and that is here. Stay tuned for more content from the archives. #aipd
HeyItsMarybeth

HeyItsMarybeth

10 likes

✨ How to: The 2-Minute Rule ✨
If it takes less than 2 minutes—do it now. 🧺 Fold the towel 📥 Reply to the message 💧 Drink your water 📋 Write that idea down 🧼 Wipe the counter Small actions → Big momentum. Discipline starts with the little things. 💡 #MindsetShift #ProductivityHack #DailyDiscipline #LevelUpRo
LuxeMindsetLounge

LuxeMindsetLounge

21 likes

4 tips on how to receive pr! ⭐️
1. Build a Curated & Consistent Aesthetic Brands want content that aligns with their identity. Make sure your feed, stories, and reels have a consistent style, tone, and quality that reflects the brands you’re targeting. High-quality photos, cohesive color schemes, and professional editing go
Raffaella ✨

Raffaella ✨

24 likes

Playing my song “Reply” for my grandma 👵🏻🎤🥺
#reaction #reactionvideo #wholesome #sadsongs #indiemusic #originalsong #lemon8music
Lindsey Jade

Lindsey Jade

387 likes

Hypnotic Aphrodite

Hypnotic Aphrodite

6 likes

Access how to get hotel collabs⬇️
Here’s where to start if you want to get paid to travel—without being an influencer↙️⬇️ Step 1: My full guide is in the first link in my bio. It breaks down exactly how I did this, so you’re not starting from scratch. Link: https://campsite.bio/thetravellingafro I started with around 2,000 fo
TravellingAfro

TravellingAfro

21 likes

Before you reply to the dry text, pause first
a steadiness object for the in-between moments. late-night text spiral, body-first interruption, pause before you reach for the phone again. #crystalbracelet #energybracelet #spiritualjewelry #protectionbracelet #manifestationbracelet #healingbracelet #chakrabracelet #dailyritual
Thunder void

Thunder void

0 likes

A smiling young woman holds a clear container filled with strawberries and blackberries. She wears a yellow tank top and a key necklace, with the text "Answering Comments!" overlaid on the image.
I’ll reply!🩵
Madison Bailey

Madison Bailey

974 likes

A social media screenshot showing comments about a person named Lori Jones being a scammer. The main text overlay states, 'just saying another x mod and look at money amount makes me sick,' and 'this is about lori jones a scammer.' One comment mentions being owed $355.
this is about lori jones a scammer
scammersbeggers.begtok

scammersbeggers.begtok

9 likes

A large pink billboard stands against a city skyline, displaying the text "Getting no message, is also a message." in dark letters. Below this, it reads "LAST TRAIN FOR PARIS." The image visually reinforces the article's theme about the significance of silence.
Silence Speaks: No Message Is Also a Message 🔑ℹ️⬇️
Not hearing back? That silence says more than words ever could. When someone doesn’t reply, it’s not about confusion—it’s clarity in disguise. A “no message” can reveal priorities, boundaries, or truths you might not want to face but need to hear. Who This Is For This is for anyone tired of o
RoadToRiches

RoadToRiches

13 likes

How to Half Swipe on Snapchat
The Half Swipe trick on Snapchat lets you read someone’s message without triggering the “opened” or “seen” status — perfect for when you’re not ready to reply, but still want to see what they said. While Snapchat has made updates over time, this method still works for text messages (not snaps or me
Lily Brown

Lily Brown

10 likes

#edit #Anime #jjk
𝓣𝓗𝓔𝓨 𝓕𝓦 𝓡𝓔𝓓

𝓣𝓗𝓔𝓨 𝓕𝓦 𝓡𝓔𝓓

1 like

You message me & I reply with this, just know....
I am siccuh you.
🇧🇧IAmDeMi23🇧🇧

🇧🇧IAmDeMi23🇧🇧

5 likes

HOW MUCH I SPEND IN A DAY! *BROKE COLLEGE STUDENT*
broke college student going broker🥲🥲 #lemon8 hope y’all liked this post! FAQ: Q: what sport do you play? A: tennis🎾 Q: what school do you go to? A: GMU Q: how old are you? A: 19 years old *i reply to all comments!*🍒🤍
Cece Liu

Cece Liu

482 likes

Looking for Durable, High-Quality Bracelet String?
Craft your perfect bracelets with our premium bracelet string—designed for strength, flexibility, and long-lasting wear. Don’t settle for less in your creations! Click the link in bio to shop now. 💎 #BraceletString #JewelryMaking #CraftSupplies #DIYJewelry #BeadSupplies
Thebeadedvault

Thebeadedvault

178 likes

🛑 Not Every Message Deserves You
Just because they reached out… doesn’t mean you have to respond. Just because they’re watching… doesn’t mean you have to engage. Not every message deserves access to you. Not every situation deserves your energy. Silence isn’t weakness… it’s a boundary. Peace is a response too. D
Grace & Growth N’ Her Healing

Grace & Growth N’ Her Healing

21 likes

🎤 “Half a Man” (Reply to “I’ve Got a Feelin’”)
Vern "CC" Carpenter

Vern "CC" Carpenter

2 likes

Dee Dee Blanchard’s altar/DeeDee’s sisters comment
#voodoo #neworleans #gypsyrose #louisiana #altar Marie Laveau's House Of Voodoo
The Tea Page With Tea 🫖

The Tea Page With Tea 🫖

7 likes

I DO NOT reply to messages
I will not reply to ANY message on this app. Man or Woman unless I actually know you. 💋
Missbizitch

Missbizitch

1 like

How to silence your mind
Phone buzzes. You look. Close it without answering. You don’t need silence. You need one tiny boundary: no instant responses for messages that reopen old wounds. Last week that rule saved me from rewriting my worth to fit someone else’s mood. I let the thought pass. I didn’t draft a
heartbreak_to_hustle

heartbreak_to_hustle

12 likes

rhode skin pt 2!
#rhodeskin #results #haileybiener #foryou #Acne
julie

julie

25 likes

WHAT I EAT IN A DAY AS A COLLEGE ATHLETE!🍋✨🎾
hope y’all liked this post! FAQ: Q: what sport do you play? A: tennis🎾 Q: what school do you go to? A: GMU *i reply to all comments!*🍒🤍
Cece Liu

Cece Liu

412 likes

My 70 cuda
imports_and_classics

imports_and_classics

1 like

A woman in a black dress is featured, with a phone overlay showing her full figure. A text box titled 'HOW TO RESPOND IN FEMININE ENERGY (INSTEAD OF MASCULINE CONTROL) WHEN HE TEXTS OR CALLS' is prominent, along with the account name @LimitlessManifestingAcademy and Lemon8 branding.
✨How to Respond in Feminine Energy …
✨How to Respond in Feminine Energy (Instead of Masculine Control) When He Texts or Calls✨ Ladies… It’s so tempting to overthink your responses when you’re in a new relationship. You want to say the right thing. You want to seem chill, confident, not “too much.” But here’s what happens when y
LimitlessManifestingAcademy

LimitlessManifestingAcademy

5 likes

Don't message me if you know you don't wanna talk
I got a lot of messages from here because I already left a link and number on my profile which people can get to me with, but I hate it when people text me and then ignores the message on my reply. It gets me frustrated and will push me to remove my link from here. If you know, you actually want to
Morgan fanpage  7️⃣

Morgan fanpage 7️⃣

17 likes

See more