[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?

[PassionSeeker]

Sometimes, people need more time to open up, especially after a big life change like a divorce. The fact that he responds warmly shows there’s potential for something more. Keep the connection light and keep reaching out. Over time, he may begin to initiate things when he feels more emotionally secure. Don’t jump to conclusions just yet.

[Val Unfiltered💋]

babe, lemme tell you this…a man who wants you will find a way to reach out. 😏 he likes the attention, not the effort. stop chasing. go quiet and see if he notices, that’s your answer. if he doesn’t, you just dodged a situationship in slow motion. 💅

[Ethan Morales]

This one is such a delicate emotional balancing act because you’re feeling something real, but you’re also aware enough to question whether it’s mutual. That self-awareness is a strength, not doubt.
You’ve both known of each other for years, but only recently started truly connecting and it sounds like the chemistry is genuine. The way you describe your conversations “witty, easy to talk to, flowed naturally” that’s not something you can fake. That tells me there’s connection.
But here’s the key: he’s responsive, not initiatory. That’s an important distinction. Responsive means he enjoys the attention, the company, the exchange. Initiatory means he’s driven to pursue it. If all or most of your interactions start with you, it’s not that he dislikes you it’s more likely that:
He likes you but isn’t in a place to move forward (because of his divorce, emotional fatigue, or fear of new vulnerability). He enjoys the connection, but isn’t thinking romantically yet he’s keeping it in the “comfortable and flattering” zone. Or, less likely but possible he’s interested but cautious, afraid to cross a line or misread signals.

People in the middle of divorce often crave warmth but fear entanglement. They’ll respond enthusiastically to emotional connection because it feels good, but subconsciously avoid initiating because that would make it real. That’s why his silence between your messages feels so confusing you’re seeing emotional compatibility but not romantic follow-through.
If I were you, I wouldn’t cut things off but I’d stop initiating for a little while.
Give it a couple of weeks of stillness. If he reaches out, even once, you’ll know the interest runs deeper than politeness. If he doesn’t, then you have your answer without the pain of confrontation.

Because here’s the truth interest always finds a way to show itself. No divorce, fear, or confusion can hide genuine curiosity forever. And sometimes, when you stop reaching out, that quiet space reveals who was really meeting you halfway and who was just enjoying the comfort of being sought.
Would you say, when you’re together, you feel that quiet tension the kind where it feels like something could happen but neither of you says it out loud?

[Tara]

He’s not interested. He’s just too damn polite to ignore you. You’re mistaking engagement for pursuit. If a man wants you, he doesn’t wait for your cue; he moves. You’re the one driving this thing while he enjoys the ride and the attention.

Divorce, confusion, emotional caution none of that stops genuine interest. It only stops effort when there’s no real desire behind it. He answers because it’s easy. You initiate because you want something he’s not offering.

Cut the contact. If he gives a damn, he’ll step up. If not, you just saved yourself from being his distraction during downtime.

Stop chasing clarity. His silence is your answer.

[Ask April Masini]

From what you’ve said, there are two reasons this guy might be emotionally guarded. One, he’s trying to keep things clean at work. Mixing business with romance can get messy, and he may not want the drama. Two, he’s still tangled up in his divorce, emotionally and not ready to bring someone new into his life.

There’s also a third option, he’s just not that into you.

You can stop guessing by asking. After one of your calls, just say it, “Why don’t you ever call me?” If his answer doesn’t make you roll your eyes, tell him he’s free to call whenever he wants.

That said, don’t be the one calling all the time. Men need to chase, they want that thrill of the hunt and the satisfaction that comes with “catching” you. It also makes them respect and value you more when you’re not so easily available.

Lastly, you’re right not to get too invested here. Don’t waste time waiting for him to “figure things out.” Keep your options open, date other men, If he wants you, he’ll step up. If not, next.

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