Hey everyone, I'm 28M, looking for some outside perspectives on this situation. I recently got out of a 9-year relationship and started flirting with this girl. I know through mutual friends/work circles. It started with light banter in late 2025, escalated to two dates in early 2026, some deep talks, physical chemistry (including a passionate kiss she initiated), but she kept pulling back due to concerns about me rebounding, our differences, and her own past (ex cheated on her). I was persistent but respectful, and after she said she expects something different, I backed off gracefully wishing her well.
The chats below show the full back-and-forth—I've anonymized names, locations, and some details for privacy (e.g., changed dates slightly, removed specific job stuff). It's long, but it captures the playful energy, her mixed signals (flirty but defensive), and how it fizzled. I pasted it all because the nuances matter.
======INTERACTION HISTORY======
December 23, 2025
Me: Kafa danas?
Her: Only if you're paying
Her: 😀
Me: If I really have to.
Her: I'm just joking
Her: I work until 17h
Her: I'm a bit sick, if you're not afraid 🤪
Me: As long as it's not COVID, I'm not afraid
Me: Then next time, some changes of plans happened.
Me: What type of job is that where you have to work on it, and until 5?
Her: Is it possible that the plans got changed 🤪
Her: I'm joking
Her: Well, I came here a bit later, so I stay until 5
Her: Until when do you work? 12?
Her: 12pm
Her: Then next year :DDD
Me: Unfortunately, I have to go with some partners, read fools, to sit…
Me: Until 3 formally, until whenever I want informally.
Her: You're like a boss
Her: 🔜
Me: Until they figure me out
Me: Then the same story, but different company 🤪
Her: Hahahahahahhahah
Around January 15, 2026
Inside a group chat we're both in, a friend asks how's my new car going. To which she says "X you've bought a car, where did you get the money". Other friend tells her "It's too late, you had your chances" – which is just a joke. She replies with "X bought me by charm since the start". I use that to invite her to a date.
Me: I'm in <her town> in Wednesday, we're going for a dinner around 7.
Me: Since I bought you, it's fair to pick up the package 🤪
Her: HAHAHAHA
Her: If it's dinner, I have to accept
Two days later, when I confirmed I'm coming, she acted like "So you're really coming", which I confirmed, and other things are logistics.
Around January 28, 2026
The first date. I picked her up, she complimented the car, she showed me images of her car. We reached the restaurant, I sat next to her. We had a basic talk about work, she was telling me about her life, her low salary, her sister getting a child, nothing out of the ordinary. During the date, I touched her on her arm several times, was getting closer to her, tucked her hair behind her ear. She didn't reciprocate what I was doing. Then, we reached a point where we were talking about another ex-college that went with her on dinner to flirt with her. I asked and what if I came here to flirt with you, to which she said it would be awkward. She continued asking whether I came to flirt with her for real. I said no. She kept asking whether it's a real no, or no just because. Then she mentions I have a girlfriend, starts asking questions about her and us. I try to dodge them. I get annoyed, and we leave. Inside the car, the moment that got me was when she asked "Did you have a good time with me?", and she asked this very shy. When I said yes, she laughed in relief. When I dropped her off, she looked me in the eyes deeply, but gave me a handshake. When she got out, she returned to tell me not to tell anyone some things she told me about her friend.
January 30, 2026
Me: <name of her friend> is mentioning that she got broken with one integration, you can see what jokes were falling on my mind 😬
Me: But with regards to formal handshake, I had to stay professional 🤪
Her: Hahahahahahh
Her: Help the girl
Her: And don't watch her pictures with her boyfriend 🤪
Me: I'm looking only where I should 😬
Me: As for your professionalism, next time I'm bringing a stamp to formalize it. And also adding an annex to the agreement that we forbid handshakes.
Her: Hahahahaahha
Her: What can you do, I'm a professional girl
Her: In difference to those who only work for 3 hours
Me: That's called efficiency, <her name>
Me: Three hours or work, two hours of planning how to avoid the handshake 🤪
Her: Maybe AI knows the answer 😀
Me: HAHAHAHAHA
Me: Fair point, now I'm gonna train one to decrypt your mixed signals 🤪
Her: Hahahahah it's really a mixed signal – I think this was ironic
Me: At least we agree.
Me: Then next time we're doing live debugging, to solve the bug 😃
Her: Hahahahahaha
Her: I didn't agree 😀
Me: Then the model made a mistake.
Me: It says that the current possibilities for green light are the largest 🤪
Her: Well, you shouldn't always listen to him
Me: Fair, but good vibration doesn't make mistakes.
Me: So, next time we're doing a 15 minute rollback, to continue from the good point.
Her: Hahahahaha oh <my name> until I figure out what you want to say sometimes
Her: Rollback from the handshake?
Me: HAHAHA, you did the good work, I didn't have to draw it for you 😜
Me: Exactly that.
Her: Oh, seems like handshake fell hard on you, it is a sign of respect, and you consistently frame it as a bug
Her: There are some bigger bugs 🤪
Me: If it's easier to call it that way, then let it be 😜
Me: I don't see any critical bugs, means we'll solve them easily.
Her: You know everything 🙂 – also ironic
February 1, 2026, late Sunday night
(I don't have this part of chat, but it was several messages where I called her on next date, nothing too important)
Me: One drink, I'm not gonna bite you.
Me: You're so hard to work with 😅
Me: Don't ruin the party with no reasons, if we think on the same bug, it's on hold for some time, so you don't need to worry about that, since I have to draw it 😃
Her: But you will 😀
Her: Hahahahahha
Her: Well we can go for a drink, but you won't change my opinion
Her: Well that's a blocker no matter what status it's in.
Me: Trust me, the situation is clearer than you think.
Me: And you are too sweet to me to give up because of misunderstanding 😜
Her: And what would want of me <my name>?
Me: First to see if the energy is real, it rarely happens that someone gets me so interested, but being so defensive 😀
Me: No pressure, just to see where this can go.
Me: Is it fair?
Her: Oh well I'm not defending, I'm just saying how it is
Her: It is fair, it is
Her: Actually it's not that I'm defending myself, you don't let me say no 😀
Me: I think that's the charm you fell for 😀
Her: Hahahahaha
Her: I was joking 😀
Her: And you suddenly took it for serious
Her: And you're sarcastic as I am
Me: HAHAHA, don't doubt you were, but it's not that wrong 😜
Her: Well now's the situation you can take it seriously
Me: So you see it's good I was persistent.
Her: I don't know if it's good
Her: If my name was <random name> maybe it'd be different – she has the same name as my ex-girlfriend
Me: If your name was <random name>, and you had that same guard and those cute bugs, I'd still be persistent the same.
Me: It's not up to the name, it's up to you.
Her: Hahahahahhah <random name>
February 2, 2026
Me: You managed to focus on the work today? 😜
Her: With regards to there not being bugs like on weekend, then I did 😀
Me: So you're focusing easier when I'm not there.
Me: I don't think I have an intent to make it easier for you that way 😀
Her: And did you manage to focus?
Her: With regards to you suddenly deciding to fall in love with me 🙂
Me: HAHAHA
Me: Don't switch it on me, you started it first 😁
Her: Oh <my name>, <my name>
Me: That oh is turning to your habit 😜
Her: Hahahahahahah
Me: Anyways, I'm there at Wednesday.
Me: We're deleting the handshake logic.
Me: And I'm closing your bugs.
Her: We're going somewhere in Wendesday?
Her: I don't know if they can be closed, they can only move to in progress 😀
Me: We're going.
Me: Then you set the status, and I'll work on implementation.
Her: We can go only by one condition.
Me: New feature request?
Me: I'm listening 😜
Her: We're going only if I'm the one driving 😀
Her: Since you drive like a maniac, I must show you how to drive
Me: You're scared of me kidnapping you?
Me: Or is there more space in the back than in <my car> 😜 – this was a reference to her comment on the first date that there is not enough space on my backseats
Her: Well now we're not even gonna go
Me: HAHAHA
Me: Seems like we aren't sarcastic the same way.
Me: Then I'm gonna calibrate mine.
Her: Yesyes yeees
Her: Nothing.. find a different time two weeks from now
Me: So, into the time-out to cool off?
Me: I accept the punishment for stupid jokes, if you change your mind I'm there to make it back.
Her: You're there…
Her: Oh, and I though you're coming just for me
Me: You know I work there, but it seems you're becoming my P1 😜
Me: Oh yeah, and P1 tickets can not wait for two weeks 😬
Me: But I accept. You drive, and I won't give comments on your driving.
Me: At least not a lot of them.
Her: I know I know you work, I'm joking 😀
Her: Hahahahahah
Her: Only the good advices
Me: I'm giving them as soon as I see our lives are in danger.
Me: Anyways, does that Peugeot have airbags? 🤪
Her: I'm not sure about that, but I know that it doesn't have backseats 🙂
Me: So even breathing in that car is luxury.
Me: I'm gonna be nice co-driver 😬
Her: Well it's because the car is luxurious itself
Me: HAHAHA, sure. I'm ready at 7, so tell me where you'll pick me up.
Her: And I have to take it to service today
Her: I forgot
Her: Hahahahahha
Her: Then next Wednesday 🙂
Me: Not gonna work.
Me: P1 incident isn't delayed due to technical issues 😜
Me: I'm taking the wheel, and I promise I'll drive like a pensioner.
Her: Okay, if it's like pensioner, but if my car is done then I'll drive 😀
Her: I'll be home
Her: Hahahahahaha
Me: Okay. I promised, I hope you don't mind people beeping us 😀
Her: They won't, when they see <my country> tables everything's gonna be clear to them
Her: Gives location
Me: Im' picking you up at 7 on station.
February 4, 2026.
The second date. I arrived at the station, got out of the car, gave her a warm hug, opened the door to her. I started driving. We had some basic talk. She asked me about the cinema and if I like it. Said that she does. We went to a caffe that was full, started walking to the other one. During the walk she said she's waiting for me to tell her what I wanted, that she's there to hear it. I said she came regardless of it. Once we sat in a cafe, she admitted she realized me liking her on first date because I sat next to her. Conversation started turning heavy, as she started interrogation about my ex-girlfriend, asking to see her picture, commenting she's very beautiful. She expressed concerns about my 9 year long relationship ending, telling me that I should wait a few months to have a clear head before dating. She was asking how do I see myself in future, the family, what do I want from life, and similar long-term compatibility questions. She was saying that we are very different and that it wouldn't work. I was till touching and cuddling her, and she accepted it. I opened up, told her I felt the need to protect her when I remembered her question if I had a good time, and similar things.
We moved to a pub to play darts, and on the way to garage, she kept insisting that I haven't convinced her about my ex-girlfriend situation. I started seeking validation at the pub, asking if she likes me, what are my red flags, etc. Atmosphere shifted when she told she wasn't sure if she liked me because of me, or because she didn't have a guy for so long. She told me she didn't date for more than a year. Her ex boyfriend cheated on her while they were living together. She says apart for him, she hasn't been on a date for 4 years. After she told me about being unsure, I told her regardless of situation, I was glad to spend time with her. I hugged her, she leaned in, I kissed her on the head.
As we walked back to the car, I didn't open the doors, and she teased me that that was the way the wind blows. Instead of taking her home, she asked for a long night ride, and told me to stop asking if she likes me. During the drive we discussed deep topics like religion and drive in life, and the moment I mentioned my ex-girlfriend as ex, she said "Oh, ex. Now you can kiss me". She admitted in the car that I was very honest on the date. She said I really annoy her when I get quiet.
We arrived to her drop off place. She asked me if I was afraid of her. I said no, but admitted that I was nervous. She said "<my name>, <my name>, what to do with you". We had intense look. She gave me a handshake again. She started to get out, but she turned her head towards me. I just looked. She moved more to get out, but turned her head again. She started to exit, but I touched her back, wanted to get her in, and she jumped on me and started kissing me. We were kissing, I bit her, and she did it 2 more times with 10 times more strength. She leaves.
That night.
Me: You were right about biting 🫣
Her: Hahhahaha
Her: I just returned it back
Her: And the second time was because you annoy me 🤪
Me: Next time I'm coming only to be quiet 😬
Her: Hahahahaha
Her: Nooo
February 5, 2026.
Me: Did you know I never kissed a girl first? 😬
Me: Until tonight.
Me: Write down one plus.
Her: Hahahahahahah
Her: But I was the one who turned back 🤪
Me: I counted two turning backs.
Me: Last time you also did it, but nothing of you 🤪
Her: What would happen if there were three 🙂
Me: Then I wouldn't let you leave the car 😬
Me: Until you stop to annoy me too.
Her: And why would I annoy you? 🤪
Her: You're not getting annoyed 🙂
Me: Because of very hard cooperation 🤪
Me: Well, you really tried 😅
Her: That was not my goal 😀
Me: So it was spontaneous 🫣
Me: No matter, you fixed the impact.
Her: Well I'm not a calculator like you
Her: Everything is spontaneous 😀
Her: Can something that's good be made better 😱
Me: But I have to decrypt you 😬
Me: Calculator says it can, especially by biting 😜
Her: What else can? 🙂
Me: Let's say a hike date, to let you talk and keep listening.
Me: On the other hand, you might get tangled if I tell you what else.
Me: But I know a lot of better ways to annoy you 🫣
Her: Not gonna work, now I have to be quiet and wise
Me: Okay, then you stay quiet until the next time.
Me: But now it's pointless to pretend 😬
Her: Oh slowly
Her: With everything in life you need to go slow, same as making decisions
Her: 🤪
Me: HAHAHA, fair, that's on you then 😜
Me: To be fair, after last night it's easier for me to be patient 🫣
Her: Well okaaay, if you say so
Her: It's good, I hardly stopped you from the topic yesterday hahaha
Her: As I said <my name> doesn't know to enjoy…
Me: HAHAHA, I wasn't glad too, but I had to, my stakes were higher 😬
Me: But add one more plus, I think I showed I know 😜
Her: If it could work like that, we'd make a deal till tomorrow
Her: Well you did, at least at the end 🙂
Me: Trust me, I wasn't up for that too, but the frame was set 😬
Me: It is much easier than negotiating 🤪
Her: Let's make it 40% negotiating and 60% enjoying 🙂
Me: I sign with condition that you don't get mad because in time it'll turn to 10-90 😜
Her: We'll see how this 40% goes 🤪
Me: We'll see 😬
Her: Just don't be afraid of me 🤪
Me: Write yourself a minus because of that try 🤪
Her: There are no more places for them
February 6, 2026
Me: Try not to bite someone on work today.
Me: Leave that for me 🤪
Her: Oooh hopefully nobody grabs me by force 🤪
Me: Better wait for me, I do it with permission 😜
Her: Okaaay I'll wait 🤪
Me: Smart.
Me: Write a plus for patience, and I'm planning v3 🤪
Her: Actually it's v2
Her: 🙂
Me: Oh, so you've become the calculator 😬
Her: Hahahaahah
Her: You're the one counting it in details
Her: Where is plus where is minus where is everything
Her: You probably know how much I weight, you calculated that too 🤪
Me: Enough small not to let others grab you by force 🫣
Her: :))
Me: Hey, I'm reserving you for Thursday.
Me: To continue to annoy you 🤪
Her: Hmmmm
Her: Oooh <my name> what I'm gonna do with you
Me: I know what I want with you 😬
Me: And I'd say you also know what you want with me 🤪
Her: Hahahahahah
Her: Well I don't knowww I told you 😀
Her: As much as I don't know English, that much I don't know this 😬
Me: HAHAHA, doesn't matter, I'll help you with translations.
Me: And I even know to read 🫣
Her: Hahahahahahahaha
Her: You know everything 🙂
February 7, 2026
Me: That's why I annoy you 🫣
Her: Ah nooo
Her: Only when you're quiet 😀
Me: Then I'm gonna be really quiet 🤪
Me: From the other side, we didn't finish one topic.
Me: Do you like blockators of silence? 😬
Her: So you actually want to annoy me? 😀
Her: Be more concrete
Me: I have to, we have good results when I annoy you 😀
Me: To lower the chances those 40% make us sleepy.
Her: Hahahahahahahaha
Her: Be bit more concrete 🙂
Me: HAHAHA, it can't be much more concrete.
Me: Maybe you don't want to be the only forbidden substance 🤪
Her: It alwaaaaays caan 🤪
Me: Oh <her name>, you're more dangerous than nice 🫣
Me: We'll leave that for in person.
Her: So it's easier to show then say 😀
Me: Better to show you, we're already well over the limit for negotiations 😬
Me: We must make up for the minus in enjoying 😜
Her: Oh I know what you think on
Her: Shame on you 🙂
Me: I don't know what fell on your mind, shame on you 😜
Her: I don't know what fell on your mind HAHAHAH
Me: Literally everything, with condition it involves you 😀
Her: Well then shame on you 🤪
Me: I got ashamed 🤪
Me: But don't worry, it'll go away till Thursday 🫣
February 9
Me: Plan change: I’m driving next time too 😬
Her: Oh boy, oh boy
Her: But I haven't changed my mind, just so you know 🙂
Her: We can grab a drink, but keep my opinion in mind
Me: Well, we have the same opinion 😬
Me: But I’m not looking for a wife.
Me: I had a better idea than just a drink 🤪
Her: And what’s that?
Her: And why aren't you looking [for a wife] :D?
Her: Which oneee? 😀
Me: Well, since we aren't "serious relationship material," we’d kill each other within three days 🤪
Me: So I’m not looking for a wife, more like an accomplice.
Me: Well, you mentioned the other day—a slightly faster pace 😬 (Note: "jaci gas" implies higher intensity/risk)
Her: Hahahahahaha
Her: Accomplice in what? In crime? 🤪
Her: Hahaha, so where are you planning to take me?
Me: In multiple crimes. You have plenty of rules we need to break 🤪
Me: I don’t know, but somewhere without witnesses 😬
Her: Ahhh, considering you wouldn’t marry me, then never mind
Me: I prefer the honeymoon over the wedding 🤪
Me: But tell me what’s on the table for a dowry, maybe I’ll change my mind.
Her: 2 chickens and me
Her: What more do you need?
Her: Oh, that’s so your style, expectedly 😀
Me: Weak offer 😬
Me: But I’ll take you for a test drive, then we’ll see 😜
Her: Depends on who you ask
Her: No way
Me: You’re being difficult to work with again 😬
Me: Don’t worry, I’ll drive carefully like last time.
Her: I’m always the difficult one :/
Her: And you think… everything is easy with Milica
Me: If it were easy with you, it would be boring 😜
Me: But you know I like "hard mode."
Her: Oh, well that is interesting
Her: Not me and the chickens
February 10
Me: Okay, we settled the chickens.
Me: Just you left, and I see it’s going to be a struggle 😬
February 11
Me: I have a feeling you’re over-analyzing.
Me: Forget the test drives and those games.
Me: I just want to see you.
Me: Tomorrow at 7 at the station?
Her: Well, I’ve already analyzed you
Her: I’ll be in the cityyy
Her: From 6 😀
Me: Well, I hope the analysis is good 😀
Me: Fine, let me know before 7 where to pick you up.
Her: <my name>, you really love making things hard for me
Her: That means I can [meet] from 6
Me: Aren't you impatient? 🤪
Me: Okay then, for 6.
Her: Doesn’t have to be exactly 6
Her: Half past 6 works
Me: HAHAHA
Me: Half past 6 it is.
Me: You wouldn't have seemed "easy" even if you stayed with 6 😬
Her: Ahahahaha that’s not the point
Me: I actually think that’s your main trick, but I’ll believe you in this case 😬
Her: But actually, I don’t even know why we’d go
Her: Because you know everything
Me: Then I know much less than you think.
Me: I’d like for us to ditch the decoding and analysis just once.
Me: To spend time and see how we actually feel in person.
Me: If we don’t click, at least we know where we stand.
Me: Because I think there are sparks.
Her: Well, I’ve already told you everything
Her: We’d go out just for me to repeat it to you again.
Me: Then I’m coming because of that 60/40, and if that’s gone, for you to tell it all to my face.
Her: Well, I’m telling you how it is
Her: So you’ll just be coming for me to tell you to your face
Me: I’m sorry you only see me through those analyses, because I see you much more clearly than that.
Me: I’m coming tomorrow because I stand by what I said about the sparks. If they really aren't there, I won't bother you anymore.
Her: I don’t think anything bad of you, I just simply expect something different
Me: I understand.
Me: I’m sorry I didn't manage to show you that you were much more to me than your analysis, and that I wasn't looking for a rebound or trying to use you. Actually, you made me want to be a good guy.
Me: Since it seems there is nothing I can do, I won’t bother you tomorrow.
Me: I hope you find what you’re looking for.
Me: And I wish you all the best, <her name>.
Her: Well, I believe you were being sincere
Her: Of course, I wish you the same 🙂
========================
After all this, I told her I respect her stance and won't bother her anymore, but honestly, I don't want to let this go—the sparks felt real, and her hesitations seem more about timing than disinterest. I've been giving space (it's been a day or so), but I'm tempted to reach out…
She made me feel something, and that didn't happen for years. I can't remove our moment from the station from my head. It was surreal for me. I never want to forget it. And I never want her to forget me.
TL;DR:
After ending a 9-year relationship, I began a high-energy, flirtatious "situationship" with a guarded woman who had been cheated on in the past. Over the course of two dates and extensive tech-themed banter, we shared deep conversations and a passionate kiss she initiated. However, she repeatedly pulled back, citing concerns that I was on a "rebound" and that we were fundamentally incompatible.
When she continued to insist that another date would only result in her repeating her doubts, I gracefully ended the pursuit, wishing her well and promising to stop "bothering" her. I am now seeking perspective on whether her interest was genuine, why it ultimately stalled, and if I should reach out again after giving her space.
Questions for you all:
- Did she actually like me? Or was I just a source of attention? The biting and the 2 AM texts felt real, but the rejection was cold.2. What is the thing that made this fail?
- What caused the fail? Was it my 9-year baggage? Or did I push too hard on the "validation" during the date?
- Future: Is there any chance for a "Version 2.0" in the future if I actually clear my head and stay single for a while? Or is this dead forever?
- Does she think about me?
- Is she going to remember me?
- What is your general view of the situation?