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Lady Whistledown's Dating Adventures

Summary:

Penelope decides that it is time to go back into the dating scene, months after her last relationship ended.

She also gets the brilliant idea to chronicle her experience on her popular gossip account.

That way, everyone can follow along, and provide (unsolicited) advice, offer (unhelpful) assistance, or simply observe (and comment on) the reaction of a certain third brother.

Notes:

For this fic, I’m heavily relying on CSS as support to tell my story. While I’ve tried to make it readable for people using screen readers, I do encourage you to read it with the Creator’s style on if you can.

Many thanks to the wonderful works I used for the layout

Happy reading!

(See the end of the work for more notes.)

Chapter Text

Lady Whistledown
@LadyWhistledown

New year, new me! Your favourite gossipmonger is finally ready to go back out there and try dating again. I want to learn more about myself, meet new people, and hopefully, by this time next year, I'll have a new beau by my side!

10:30 · Jan 5, 2026


43 Retweets    84 Quote Tweets    4.1K Likes


Lady Whistledown @LadyWhistledown · Jan, 5 Replying to @LadyWhistledown

Worry not, dearest reader, I'll continue to tell you all the gossips I hear through the grapevine, including those caught on dates. But, in addition to that, you'll also hear about my foray into dating. Maybe that should worry you... I know it scares me 😶

 


 

Text message chat with: El 🌼

El:Saw your tweet 10:46

El:Ready to date again? 10:46

El:Finally over Alfie? 10:47

Pen: I've been over him for months now 10:48

Pen: The problem was/is more the low self-esteem he left me with 10:48

Pen: Still working on that 10:49

Pen: But as my therapist says: going back out might help me with that 10:49

El: As long as you remember that the men are shitty, not you 10:50

Penelope reacted with: ❤️

Pen: With a best friend like you, how could I forget? 10:50

 

 


 

Text message chat with: 🪻 Hyacinth 🪻

Hyacinth:DAPH!! 11:04

Hyacinth:did you see penelope's tweet?? 11:04

Daphne: I hadn't 11:06

Daphne: Who should we set her up with? 11:06

Hyacinth:???? 11:06

Hyacinth:COLIN 11:06

Hyacinth:what kind of dumb question is that???? 11:06

Hyacinth:were you drop on your head as a child??? 11:06

Hyacinth:was it ben? or ant? 11:07

Hyacinth:or colin when he heard there were biscuits 11:07

Hyacinth:it was probably colin, and now the universe is getting back to him with you asking dumbass questions instead of setting up with the love of his life 11:07

Daphne: No, no I know we need to set them up 11:08

Daphne: I'll always be team #Polin 11:08

Hyacinth:ok, i'm all for polin, but please don't use the literal hashtag 11:08

Daphne: But I don't think it's a good idea to officially set them up this early 11:09

Daphne: Penelope should go out a bit, gain some self-confidence, make Colin jealous, enjoy herself 11:09

Daphne: And then, when the moment's right (and Colin's really miserable), we strike 11:10

Daphne: We might have to hold Colin's hand to make him realise his feelings for her too 11:10

Hyacinth:ok, i know when i should admit that i was wrong 11:10

Hyacinth:that's an acceptable plan 11:11

Daphne: Of course it is 11:11

Daphne: Do you think one of Simon's boxing friend would suit Penelope? 11:12

Hyacinth:and we're back to dumb ideas 11:12

Daphne: What! Why? Colin hangs out with them sometimes, it'd make him jealous 11:12

Hyacinth:penelope doesnt like sports or violence, why would she want to date a boxer? 11:13

Hyacinth:she always judge the guys when they talk about it, even colin 11:13

Daphne: I hadn't noticed 11:14

Hyacinth:of course not, you always drool at simon when he talks about it 11:14

Hyacinth:but penelope doesn't think it's hot like you do 11:15

Daphne: Maybe it's because she's never seen Colin fight? 11:16

Hyacinth:akskskdkfjansnf 11:53

Hyacinth:youre really dumb 11:53

Hyacinth:remember how her dad got in trouble with the law because he tried to fix boxing matches 11:53

Daphne: Oh 11:56

Daphne: I'd forgotten, I'll find someone else 11:56

 


 

Lady Whistledown
@LadyWhistledown

Sometimes I forget that while most of you don't know who is hidden behind this account, some people in my real life do know who I am... 🤦‍♀️
@ /Mum: my last tweet wasn't an invitation for you to set me up on dates

16:38 · Jan 5, 2026


45 Retweets    63 Quote Tweets    4.5K Likes

 


 

A group chat called: The Wise Women with: Eloise, Edwina, Gen, Penelope

Gen Delacroix
Who did Portia come up with? 16:41

Edwina Sharma
And what did the wedding invites look like? 16:43

Pen: 😭😭😭 16:43

Pen: You'll never guess who she came up with 16:44

El 🌼
The mailman? 16:45

Gen Delacroix
Her aquagym instructor? 16:45

Edwina Sharma
Her 90 yo neighbour? 16:45

Pen: 😭😭 somehow worse than all three 16:46

Pen: The plumber's son, whom she's never met 16:46

El 🌼
Portia, please never change 16:46

Edwina Sharma
Did she know his name at least? 16:46

Pen: It's either Mark or Steve 16:47

Pen: You might think, like me, that these names sound nothing alike, but my mum assures me they're very similar 16:47

El 🌼
Knowing her, it's neither 16:48

Pen: She also doesn't know anything else about this Mark/Steve, but his father looks good enough for his age, so she expects that his son will age like him and therefore I should date him 16:49

Pen: That should be enough to convince me, right? 16:49

Gen Delacroix
I love your mum 16:50

Edwina Sharma
I'm so glad she's not my mum 16:50

 


 

Text message chat with: Pip Finch

Pip: Just went to mum and she told me how you want to date again 20:39

Pen: I should've blocked her from my twitter account 20:46

Pip: She'd make a new secret account 🕵️ 20:47

Pen: True 😫 20:47

Pip: Anyway, I think I've convinced her you weren't being ungrateful when you refused to go out with her plumber's son. She still doesn't understand why you said no 😔 20:48

Pip: And then, Albie and I talked about it on the car back home and we think we know someone who would fit you 💞 20:48

Pip: You remember Lewis? 🌞 20:49

Pip: He's Albie's friend, really sweet. He can be a bit shy, but once you get to know him, he's really attentive and nice. He was at our wedding, maybe you've met him already. That would be a cute story at your own wedding 🕊️ 20:49

Pen: Maybe later? I want to try on my own first 20:50

Pip: How ungrateful 😜 (I'm only joking!! I'm really excited for you!!!) 20:51

 


 

A group chat called: Surviving the 🐝's with: Kate, Sophie, Penelope

Sophie Baek
When you say you don't want your mother to set you up on date, does it mean we can? 9:26

Kate Sharma-B
Yes! I have someone in mind for you 9:37

Pen: Please don't. At least not yet, I'm trying to do it on my own for now 9:41

Pen: Putting myself out there alone, calling for the universe to bring me the perfect man 9:41

Sophie Baek
Wishing you all the best on your endeavour! 9:44

Kate Sharma-B
You deserve nothing but the perfect man! You've got it 9:58

Kate Sharma-B
And let us know if you ever change your mind 😉 9:58

 


 

Text message chat with: Kate Sharma-Bridgerton

Sophie: Is the guy you have in mind Colin? 10:03

Kate: I mean yes. But I don't think either one of them are ready for that quite yet 10:04

Sophie reacted with: 😔

Sophie: I know... 10:05

Kate: But there's a guy at the stables where I ride. I feel like they could get along 10:06

Sophie reacted with: 👀

 


 

Lady Whistledown
@LadyWhistledown

I've been out of the dating scene for a little while and I had forgotten how awful it is. Setting up a dating profile is really a humbling experience.

Receiving messages from men is a soul-crushing one.

14:37 · Jan 6, 2026


64 Retweets    78 Quote Tweets    3.4K Likes


Lady Whistledown @LadyWhistledown · Jan, 6 Replying to @LadyWhistledown

When I say soul-crushing, fear not: it's not about me. It's about the realisation of the deteriorating quality of men out there. Maybe I do need to take my mother up on her offer (Mum, this is a joke, no I don't want your help)


Lady Whistledown @LadyWhistledown · Jan, 6 Replying to @LadyWhistledown

My mum just texted me an ominous "Yet."

That's the scariest message I've received today, and I've been talking to men all day

 


 

Text message chat with: Pru Dankworth

Pru: I know you're joking, and I know you wrote in your tweet that you were joking, but please stop 19:08

Pru: Harry and I had to spend five minutes talking mum down from texting her plumber about his son because of your last tweet 19:08

Pru: Can't you block her? 19:09

Pen: Urg sorry about that 19:21

Pen: As Pip said: if I were to block her, she'd make a secret account to spy on me 19:21

Pen: I'll talk to her... again 19:22

 


 

Lady Whistledown
@LadyWhistledown

I know you love my gossip because I usually give out names. Today will, sadly, be the exception, for my own personal anonymity. But worry not, the tea is scolding hot nonetheless 🍵

15:42 · Jan 8, 2026


21 Retweets    19 Quote Tweets    986 Likes

 

Lady Whistledown
@LadyWhistledown

Earlier, I ran into my ex – who broke up with me less than a year ago to go on a two years work trip away from London – on a date with my old school bully.
At least I know I won't find a shittier man than that.

17:30 · Jan 8, 2026


34 Retweets    49 Quote Tweets    2.5K Likes

 


 

Text message chat with: El 🌼

El:ALFIE AND CRESSIDA???? 17:42

El:🤮🤮🤮 17:42

El:You should put trigger warnings on your tweets 17:42

El:I hated both of them before, it's even worse now 17:43

Pen: At least he looked super uncomfortable running into me 17:44

Pen: He tried to drop her hand when he saw me, Cressida had no shame 17:44

Pen: He knows how much she bullied me, we talked about it 17:45

El:What an asshole 17:45

El:At least now he's dating someone he deserves: worse than the devil 17:45

El:Do you know why he's back in London already? 17:46

Pen: He didn't tell me, but I looked it up 17:47

Pen: His expedition was a failure, he stayed there 3 months before they ran out of money and investors refused to fund it any further 17:47

Pen: To say he wanted me to come with him 17:47

Pen: Tbh, it boosted my ego to run into them: he's a failure of a man, dating the worst person in the world, while I'm living my best life, trying to find love again 17:47

Pen: And I got a good post for LW 17:48

El:THAT'S THE SPIRIT 💪 17:48

El:You deserve love from a good man, not someone like him 17:49

 


 

Text message chat with: Mum

Portia:Alfie broke up with you? I thought you did! 17:56

Portia:And you were bullied in school? Why didn't you tell me? 17:56

Pen: I changed things for the tweet. You know what really happened 17:59

Pen: Our relationship was already struggling when he got his grant for his research in Antarctica. He offered me to come with him and told me that he was not interested in doing long-distance. I told him I wasn't going to follow him, away from my family and friends, with no job for me. I didn't want to wait the whole day in the middle of nowhere while he watched penguins for 2 years. So, we mutually agreed to break up 18:00

Pen, replying to: Mum
And you were bullied in school? Why didn't you tell me?

Mother, I was an insecure short and chubby child, I was liked by my teachers and had effortlessly good grades: I was an easy target. And then everyone found out about dad's mishaps with the law. So yeah, of course I was bullied. I thought it was a given 18:00

Pen: You were also dealing with divorcing him and trying not to get kicked out of our house while trying to protect us. I didn't think I needed to bring it up to you 18:01

Portia:💔 18:14

 


 

Lady Whistledown
@LadyWhistledown

Why is the new big date idea is going bouldering?? It's the third time someone mentions that for a first date. And don't tell me it's because it's a good way to build trust. Why would I trust a man who takes me bouldering on a first date????

13:38 · Jan 10, 2026


34 Retweets    67 Quote Tweets    2.4K Likes


Lady Whistledown @LadyWhistledown · Jan 10 Replying to @LadyWhistledown

I am now getting flashbacks from when we went abseiling on a school trip, I still wake up in cold shivers at night. I truly hope all pictures from that experience have been burnt down.

I might have screamed at the guy securing me while I was climbing down – I do not recommend

 


 

Text message chat with: El 🌼

El: A still from Derry Girls, when Nicola's character, Clare, goes abseiling. 13:56

Pen: Go die 13:59

El:Love you too ❤️ 14:07

 


 

A group chat called: Bridgerton bros with: Anthony, Benedict, Gregory, Colin

Gregory
Just saw Penelope's tweet 14:25

Gregory
Is bouldering really a bad date idea? 14:25

Benedict
Greggy, who are you taking out on dates? 14:28

Anthony
I wouldn't do it on a first date: do something more classic like a good restaurant where you can get to know her. Then, later on, when you know whether or not she enjoys that kind of activities, sure, you can take her boudlering 14:34

Anthony
Kate and I have gone once to try it out, but we were already married 14:34

Gregory
Ok, thanks Ant 14:35

Benedict
Don't ignore me Greggy! 14:36

 


 

Text message chat with: Violet Bridgerton

Violet:Dear Penelope,
I saw how you're starting to date again. 🌷
It is a very brave thing to do, especially in front of an audience like you are doing. You are a star! 🌟
I know from personal experience how difficult it can be to start dating again, and I wish you all the best.
Let me know if you need to talk, about this or anything else.
🩵
Violet 17:19

Pen: Thank you Violet ❤️ 17:23

 


 

Text message chat with: Colin 🍪

Colin:Hey Pen! Back on the grid after a week in the cold but magnificent Scandinavian tundra 15:27

Colin:Hope you're doing well! 15:27

Pen: Colin! Good to hear back from you, I hope everything went well, can't wait to hear all about it 15:29

Pen: And to read what you've written about this experience when it's ready! 15:29

Colin:It's still just scribbles in my notebook at the moment, I'll probably work on that more properly when I'm back home 15:30

Colin:I'll let you know when it's ready! 15:30

Pen: Please do! And let me know when you're back in town, we need to catch up! 15:30

 


 

A group chat called: Bridgerton family with: Violet, Anthony, Benedict, Colin, Daphne, Eloise, Francesca, Gregory, Hyacinth

Colin: Back on the grid! Hope you're all well and that I didn't miss too much 16:03

Colin: A week in the tundra was a really cold, but fantastic experience, I encourage you all to do it at least once 16:03

Mum
Hello Darling, Welcome back 🩵
Xx Mum 16:04

Anthony
Great to hear! Are you coming back to London already or do you still have some travelling to do? 16:07

Daphne
Bel asked me non-stop if you were with penguins 😂 16:10

Daphne
We can't wait to see you! 16:10

Colin: No penguins sadly, I'm not Penelope's ex 16:13

Colin: I can't wait to see you all, partners and niblings obviously included! 16:13

Colin: @Anthony: I have two days in Oslo and then I fly back home 16:13

Gregory
ran into Tessa's sister at a party, Tess' engaged now 16:17

Benedict
Colin's old gf? How do you remember her? You were like 3 when they dated 16:18

Gregory
I was 7, and in the same class as Connie, so I remember 16:18

Eloise
Why are you bringing her up like that? 16:21

Gregory
Colin was asking what he'd miss, I told him 16:22

Colin: Was not really thinking about updates on my first girlfriend when I asked if I'd missed anything, but good for her 16:26

Hyacinth
something much more important that you've missed is that penelope is dating again 16:28