I Waited 7 Years to Ask My Best Friend Out. It Was a Mistake

[Blessing]

Tobi* (25) fell hard for his best friend of 14 years, and what started as a simple friendship slowly became years of quiet longing, jealousy, and heartbreak. He opens up about how his unspoken feelings affected other relationships, and how waiting too long cost him both the romance he wanted and the friendship he cherished.

From Friendship to Longing
Tobi and Mimi* have known each other since childhood. Their families were close, they attended the same church, and later the same boarding school in Osun. While Mimi was charismatic and popular, Tobi describes himself as the quiet, awkward boy she always defended. By the end of secondary school, Tobi realized he liked her but he didn’t act on it.

Instead, he began dating Ann*, a girl from their church, hoping it would help him move on. Their relationship lasted nearly three years. Everything went smoothly until Ann received a scholarship to study in the Netherlands. The long-distance strain, combined with a pandemic, led to their quiet breakup, leaving Tobi heartbroken.

Reconnecting With Mimi
After Ann left, Tobi and Mimi reconnected. They spent Sundays together after church, and his long-buried feelings returned. But Mimi soon entered another relationship with Idris*, an older man with financial stability but controlling tendencies.

Tobi stayed close to Mimi, supporting her emotionally as she faced challenges in that relationship. One night, overwhelmed by his feelings, he even pretended to be her to end her relationship with Idris via text. The move backfired, causing tension and embarrassment, but Mimi eventually forgave him.

Despite this, she continued to pull back to protect her relationship. Tobi, desperate to move on, started dating Mercy, whom he met on Bumble. But his unresolved feelings for Mimi sabotaged the relationship. Mercy ended things after seven months, leaving Tobi confronting the reality that his attachment to Mimi still controlled him.

Confession and Consequences
In November 2024, Tobi finally confessed his love to Mimi, expecting clarity. Instead, she told him she had never thought of him that way and was still healing from her breakup. Their friendship became awkward, and she eventually started dating someone else. Tobi describes the pain of watching the connection he had built over years slip away.

To cope, he moved temporarily to his company’s Ibadan branch, creating the distance needed to start healing. Today, he and Mimi speak occasionally, but their relationship is limited and platonic.

Lessons Learned
Tobi has learned painful but valuable lessons about love and timing. He emphasizes the importance of honest communication:

“If you feel a certain way about someone, just say it. It helps you move on faster, even if it doesn’t go your way.”
He reflects on how attachment and fear of rejection delayed his heartbreak and ultimately cost him other opportunities, like a potential relationship with Mercy.

Life Now
Tobi rates his current state at a 7/10. He’s no longer stuck waiting for someone who doesn’t reciprocate his feelings. It’s painful but liberating. Slowly, he’s rediscovering his identity outside of Mimi and learning to separate love from obsession.

“I built my entire emotional life around her, so letting go hasn’t been easy. But I’m taking my healing slowly and learning to value myself first.”

[Author]

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