[claire_returned]

I’m in my late 30s and moved back to my hometown about two years ago. Through work I kept bumping into a man my age who grew up in the same neighborhoods and even went to the same schools — someone I’d seen around my whole life but hardly knew. For years our interactions were tiny: quick “hi, how are you?” exchanges at his workplace, nothing that made me think there could be anything between us. Once, I even thought he was avoiding eye contact.

About a month ago I called him for some professional advice and he came by my office. After we wrapped up, he initiated the first proper conversation we’d ever had. I was surprised — he was witty, easy to talk to, and the evening flowed naturally. On a whim I invited him over for a drink and he said, “sure, anytime.” Since then we’ve had long phone calls, witty texts, and a couple of relaxed meetups. He did come over for drinks and it was a lovely night.

Here’s what troubles me: almost every contact has been started by me — sometimes blatantly, sometimes under the pretense of work. He answers enthusiastically and participates fully, but he never reaches out first. Some days I convince myself there’s a romantic spark; other days I tell myself it’s friendly curiosity. I also know he’s currently going through a divorce, which could explain emotional caution or conflicting signals.

I don’t want to pour time and feeling into something that will remain a pleasant friendship. Has anyone been in a situation where someone responds warmly but never initiates? Is his silence a sign he’s not ready for more, or should I keep investing time and risk getting attached? What would you do?

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