Advice appreciated- am I overreading this - a male friend (met at work) complimented me on my looks, introduced his girl friend to me the first year, invited me to an engagement celebration but his fiancé ended the relationship. He checks in on me once in awhile asking me how I am (almost like he wants to get to know a bit more personally) but doesn’t ask to meet? I can tell he’s curious. But I don’t know what to do with it.

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Are you sure he is single? Are you romantically interested in him? Are you single? How closely do you two work together at your company? The answers to these questions should help you decide among your options.

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He’s single. I think he’s cute. We don’t work at the same firm anymore. Like it’s been two years since we last met but we are in the same city. He messages me few times a year and it’s really awkward because I can’t tell why he asks certain questions and goes quiet. He’s a few years younger than me and I’ve seen him on few dating apps.

Are you looking for advice? What's the question?

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Am I overreading into this situation was my question haha

I would say, don't overthink it. Series of questions you should ask yourself: are you interested in getting to know him better? No, then stop thinking about him or his texts. If yes, then ask him if he wants to catch up in person over coffee or a drink. Then take it from there. Sometimes we focus so much on whether the other person is interested in us, when you should be first asking yourself whether you are interested in him (no matter how often he does or does not reach out, whether he is on apps or not, etc)

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I take no man seriously until they express explicit interest and ask to take me on a proper date. We value directness, and men that know what they want over here!

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If you’re interested, ask him out. If you’re not interested, ignore him.

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This

How long ago did the engagement end, and how long were they together? If it's been less than 6 months since the engagement ended, I think you can try to be closer friends with him, but I wouldn't expect any big commitment out of him. You can drop hints and spend more time together if you think he's "curious" but I would try to steer clear of chasing him (which is a fine line)

You also need to ask yourself what do you want from this scenario?

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Yeah I think that’s the word.

Just ask to catch up over a drink. Done.

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Do you hang out outside of work?

Then I’d just consider him a work friend … not an actual friend.

If you’re matching his energy / interest, then in IMO, he would have asked you to grab coffee or a drink if he was truly interested.

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Since he invited you to his personal life events, he considered you a friend. Checking in on friends casually from time to time is very normal.

But, it sounds like you may be interested here now that he is single. The ball is in your court. It’s been a year since his break up, maybe he is over her.

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