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AITAH for proposing to my girlfriend ‘so soon’ after my ex and I broke up?

by Michael Lee
October 28, 2025
in Relationships
Reading Time: 6 mins read
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For four years, he and Chloe built a life filled with love, dreams, and shared moments, only to have it unravel under the weight of an ultimatum that forced a painful choice between love and personal ambition. Their final year was a storm of misunderstandings and heartbreak, marking the end of a chapter that neither was truly ready to close.

In the aftermath, he faced not only loneliness but also the harsh judgment of being cast as the villain in a story he never wanted to be part of. Yet, from the ashes of that painful past, a new love blossomed—Gabby, who brought light and hope back into his life, culminating in a promise of forever that once seemed impossible.

AITAH for proposing to my girlfriend ‘so soon’ after my ex and I broke up?

I (31M) dated Chloe (29F) for 4 years until we...

and she basically gave me an ultimatum to either propose...

I have a business I couldn't just abandon, and I...

Our last year together was full of fights and miscommunication....

A year after we broke up, I started dating Gabby,...

We've been together for 2 years now, and we've been...

That's when all h**l broke loose. Not even 12 hours...

I get a call from Chloe, frantic and screaming at...

and saying I wasted her "fertile years." She kept going...

Since then, I've been getting nonstop calls and hateful messages...

sending really nasty comments, and wishing harm on her. Our...

I went to my mom to vent, and she basically...

and that it would definitely reopen old wounds for Chloe....

I ended up leaving her house without saying goodbye, and...

All my friends are on my side, but my mom...

Gabby is also upset because our happy news has been...

As renowned relationship therapist Esther Perel explains, ‘When we are entangled in the past, we forfeit the present.’ This situation clearly illustrates a breakdown in establishing necessary emotional distance following a difficult separation, where one party’s attempt to fully embrace a new future is met with resistance rooted in the unresolved grievances of the past.

The OP’s relationship with Chloe ended three years prior due to fundamental incompatibilities and an ultimatum. The OP’s subsequent relationship with Gabby progressed naturally to engagement. Chloe’s extreme reaction—labeling the OP a ‘cheating bastard,’ attacking his character, and involving mutual acquaintances to harass the new fiancée and damage the OP’s business—suggests an inability to process the finality of the breakup. Her accusations about ‘wasted fertile years’ indicate a deep-seated feeling of loss and victimization that she projects onto the OP’s current joy.

The mother’s siding with Chloe introduces a complex dynamic of triangulation and perceived betrayal for the OP. While the OP’s timeline (four years with Chloe, two years with Gabby, engagement now) is not inherently rash, announcing the engagement so publicly right after an ultimatum-based breakup likely acted as an unexpected trigger for Chloe. Professionally, the OP’s actions regarding his engagement were appropriate for his relationship with Gabby. However, the constructive recommendation is for the OP and Gabby to implement strong, unified communication boundaries: block Chloe and her associated contacts, report harassment regarding social media and business reviews immediately to the relevant platforms, and refrain from engaging with Chloe’s narrative, thereby establishing clear distance and protecting their present happiness.

What do you think of this story?





THIS STORY SHOOK THE INTERNET – AND REDDITORS DIDN’T HOLD BACK.

Dipshitistan Proposing to another woman THREE YEARS after breaking up...

What the actual f**k?!? NTA, but your ex is certifiable...

SilveryCookie NTA. You're not responsible for how Chloe processes your...

You've moved on, built a healthy relationship with Gabby, and...

Chloe's reaction is over the top and unreasonable, and the...

Hara*sing you, Gabby, and your business crosses so many lines...

Your mom's perspective seems to be based on misplaced empathy...

but you're not obligated to put your life on hold...

The fact that you and Chloe weren't on the same...

let go. Focus on celebrating your engagement with Gabby,

and consider taking steps to block Chloe and her friends...

If things escalate, you may need to consider legal action...

Don't let their negativity overshadow your happiness you're not in...

Chaoticgood790 It's been 3 years these people are psychotic. Have...

You should be able to flag the influx of reviews...

These people are idiots Also please check your mom hard...

MIL). Ask her how long you were supposed to be...

Wooden_Television701 Your ex left you she can kick rocks: Lawyer...

Infamous_El_Guapo hara*sment and sketchs reviews is NOT IT: So your...

Gabby (her soon to be daughter-in-law) and that your ex's...

and she's not on your side? I get a bit...

Why isn't she engaged after 3 years?

I'd suggest a follow up conversation with your mom about...

VegetableBusiness897 Sounds like Chloe has been continuing to waste her...

nycguy1989 Wonder why that is?? Couldn't possibly be a her...

that'll be hilarious NTA. Your ex is ridiculous and so...

The original poster (OP) is facing significant emotional fallout after announcing his engagement, as his ex-partner, Chloe, and even his own mother, believe his actions were insensitive and hurtful to Chloe. The central conflict lies between the OP’s right to move forward happily with his current relationship and the perceived obligation to minimize the distress caused to his ex-partner regarding the timing of his engagement announcement.

Was the OP wrong for celebrating his happiness without anticipating or mitigating the severe, prolonged reaction from his ex-partner and her circle, especially given his mother’s reaction, or is the responsibility for managing Chloe’s feelings solely hers now that the relationship is long over? The core debate centers on where personal celebration ends and consideration for past partners’ emotional states begins.

Michael Lee

Michael is a tech enthusiast sharing insights on software development and gadgets.

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