My Casual Office Affair Took an Unexpected Turn

A 24-year-old woman shares that she’s been hooking up regularly with a male coworker who sits just across from her. Their dynamic has been strictly professional in the office, but once he slid into her DMs, the intimate tone shifted. They met for drinks one evening, he walked her home, and what followed in her room was the start of a weekly ritual—intense, physical, and initially emotion-free.

But during a recent barbecue, she was kissed by one of his male friends. Word reached her office lover, and everything changed. He’s become more caring—checking in on her, engaging in deeper conversations—and she’s wondering if this means uncomplicated passion is evolving into something more meaningful. She worries it might simply be a ruse or a typical player move, and fears to ask outright in case she appears needy or overthinking things.

Deidre’s response: That kiss may have been an emotional catalyst for him. But to truly understand where they stand, she needs to have “the conversation”—not a dramatic sit-down, but a casual check-in like, “How do you see us?” It’s reasonable, she says, to seek clarity.

If he makes it clear he’s not looking for commitment, she needs to decide what she wants. If she’s falling for him, she may need to step away. And if being just “friends with benefits” works for her, that’s okay too—so long as she’s honest about her emotional boundaries and doesn’t make room for more heartbreak. Ultimately, she’ll learn soon if he’s ready for exclusivity—or if she’ll find someone who is.

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