A man’s world flipped upside down when his two-year romance blossomed into an engagement to the very woman who once supervised his ex-wife. What started as a casual club conversation with his buddy turned into something serious, catching everyone off guard. Now, with two children shared from the decade-long marriage and a wedding date set, the ex-wife crumbles, pleading with him to end it and pick someone, anyone else.
In desperation she sends him photos of her single friends, hoping to sway his choice, but he stands firm, declaring the past is over and his future is his own to shape. The tension hangs heavy as family ties clash with workplace shadows, leaving everyone wondering if this unlikely union will hold or unravel everything in its path.
Man plans to marry ex-wife’s boss after two-year relationship.
Love doesn’t always follow neat boundaries. People meet in unexpected places, and after a decade-long marriage ends, moving on with someone new is a personal right.
The Redditor emphasizes that he only met her once before the divorce, and their connection sparked organically later. Many see no major issue here: he’s free to date whoever he wants, and the relationship has thrived for two years without apparent workplace fallout.
Yet flip the perspective, and the discomfort is real. The ex-wife faces a daily reminder of her past marriage through someone who controls her career, paycheck, and work environment.
Commenters point out the power imbalance: what if roles were reversed and she dated his boss? The unease about potential favoritism, bias, or even subtle pressure is valid, even if unintentional.
This a classic workplace conflict-of-interest scenario. According to the Society for Human Resource Management (SHRM), while workplace romances are common, with over 60% of adults having experienced one at some point, per Forbes Advisor research, relationships involving supervisory roles often require disclosure to mitigate risks like perceived favoritism or harassment claims.
Broadening this out, family dynamics after divorce already carry enough tension. Add a professional power dynamic, and it can amplify feelings of betrayal or insecurity.
Studies show that ongoing contact with an ex-spouse can heighten psychological distress post-separation, especially when children are involved.
Here, the boss’s role in the ex-wife’s livelihood creates an unavoidable layer of ongoing “contact” through employment, which can feel invasive and amplify post-divorce stress, especially with children involved where high-conflict dynamics often heighten emotional strain.
According to Chelsea Mesa of Seyfarth Shaw, as quoted in Risk Management Magazine, “An organization’s policy regarding office romances should address potential conflicts of interest or the dissemination of confidential information”.
While this isn’t a direct supervisor-subordinate romance, the indirect tie through the ex-spouse raises similar ethical flags, many HR professionals would flag it as problematic enough to warrant reassignment or transparency, as policies often focus on mitigating risks like perceived favoritism or legal exposure.
The neutral takeaway? Relationships thrive on mutual respect and clear boundaries. The couple could explore solutions like the fiancée stepping back from direct supervision or full HR disclosure to protect everyone.
Open communication with the ex about co-parenting priorities might ease some hurt, too. Ultimately, love is personal, but when careers and kids intersect, a little extra empathy goes a long way.
Here’s the comments of Reddit users:
Some people believe the OP is NTA for dating whoever he wants, as personal relationships are his choice.
Some people consider the OP an AH or at least insensitive for dating his ex-wife’s boss, seeing it as deliberately uncomfortable or petty.
Some people view the boss as the main AH for not disclosing the relationship to HR or the ex-wife, creating a major conflict of interest.
Some people suggest the boss should step down from supervising the ex-wife to resolve the power imbalance.
Do you think the Redditor’s choice to move forward with the marriage is fair, considering the family and professional stakes involved, or does the workplace connection cross an uncomfortable line?
How would you handle introducing a new partner who’s tied to an ex’s career? Drop your thoughts below!
