AITA for dating a guy whose “best friend” is his ex who refuses to meet me?
Ten months into an otherwise great relationship, my boyfriend’s ex—and current business partner—won’t meet me, dodges events, and spiraled when I got close. It went from quirky to frighteningly suspicious.
I (25F) started dating Jeff (26M) and quickly learned his “best friend” Jenna (20sF) is also his cofounder. Early social media sleuthing showed couple-y photos and captions like #relationshipgoals; he later admitted they dated for nine months, broke up a year and a half before we met, then launched a business together. I met everyone in his life but her. Every near-meeting evaporated—she’d just left the office, or he’d meet me outside so I wouldn’t go in. The pattern escalated the night of their open house: he parked me at a coffee shop “to kill time,” then texted that Jenna had a “family emergency.” Afterward he confessed she’d had a panic attack and fled because she was “scared to meet me.”
I fell for Jeff and saw a future, but his ex—who’s also his business partner—kept dodging me, panicked when I was nearby, and even made him reroute us to avoid crossing paths. I felt disrespected, suspicious, and like a shadow in my own relationship.
We’re 10 months in; he’s 26, I’m 25, Jenna’s mid-20s. He and Jenna dated for nine months, broke up ~18 months before us, then became best friends and co-owners. I met friends and family quickly—but never her. At events she “couldn’t make it,” at the office she’d “just left,” and once he steered me to a coffee shop instead of letting me help them set up for an open house.
“While they were getting ready, she had a panic attack and said she was scared to meet me.”
I raised my discomfort; he apologized and admitted he was mad at her but “didn’t know what to do.” More incidents piled up: he walked me around the block to avoid her when she was still in the office; she skipped a party solely because she didn’t know if I was there; she sat outside his place texting while his phone was dead. Then he left for a pre-planned two-week camping trip with her—while her Instagram kept filling with new photos of him.
“I felt like Jenna was his real girlfriend and I was the secret.”
A year later, distance for a work contract magnified everything; I checked her posts daily and felt miserable. When I returned, I broke up with Jeff, telling him his boundary-less friendship with Jenna made our relationship untenable—cheating or not. Months passed. Then he called, apologized, said the dynamic felt toxic, and moved to dissolve their business partnership. We met up; he unfollowed her and cut contact. Six months later, we’re back together, ran into her at a concert, and they didn’t even say hello. I feel respected in a way I didn’t before.
🏠 The Aftermath
I ended the relationship; he later recognized the toxicity, ended their business partnership, and went no-contact. We reconciled after months apart.
He unfollowed her on social media and hasn’t spoken to her in six months. We even crossed paths in public and they didn’t acknowledge each other. Day-to-day, our relationship feels calmer and more secure.
The big shifts: no more triangulation, fewer fights, and a rebuilt sense of respect. The cost: he lost a business partner; I regained peace of mind.
Boundaries fixed what reassurance couldn’t.
I’m relieved more than vindicated. It’s strange that it took a breakup to clarify priorities, but the reset finally matched actions to words.
💭 Emotional Reflection
This wasn’t a simple “jealous girlfriend” story. It was a mismatch of boundaries: he believed history plus business could coexist; I needed transparency and inclusion. Jenna’s avoidance and fixation made normal integration impossible, and his neutrality read as complicity.
Breaking up forced a choice he’d been postponing. By ending the partnership and contact, he showed whose needs took priority. It’s a reminder that reassurance without action rarely heals insecurity sparked by real behavior.
Reasonable people may disagree—some can manage close friendships with exes, others can’t. But it only works if everyone respects boundaries and the current partner isn’t made to feel like the outsider.
Readers had strong feelings about the ex-as-best-friend dynamic:
NTA — Her refusal to meet you and the secretive rerouting were giant red flags. Your breakup set a healthy boundary.
ESH-lite — Jeff should’ve enforced boundaries sooner, but credit for eventually dissolving the partnership and going NC.
You can be friends with an ex, but not at the expense of your current partner’s sanity and inclusion.
Overall, commenters focused on boundaries, transparency, and the difference between reassurance and action. Many felt the reconciliation only worked because Jeff finally acted, not because the feelings magically changed.
🌱 Final Thoughts
Partnerships thrive on inclusion. If you keep someone central in your life who undermines your relationship, you’re making a choice—even if you pretend you aren’t.
Once words matched behavior, respect came back. Sometimes love needs a hard reset to be healthy.
What do you think?
Would you have left, or stayed and kept trying to make it work? Share your thoughts below 👇
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