I will never run into her randomly unless I stalk her so I went ahead and texted. I said I heard about the divorce, offered condolences, asked how she was doing. She said it's been hard. I agreed that it must be and I told her I'd been thinking about her and hope she was ok. She said she appreciates it.

That's it, I'm going to leave it at that. Maybe check in again in a month or two. She didn't seem excited to hear from me so it's either still too early or she's not interested. Either way I don't think I overdid it and what I said was completely appropriate given the circumstances.

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Well played 🤙

I think it's good you kept it light.

Desperate vibes from you, my dude.

I'm not desperate, but I know that's how it might look which is why I was seeking advice on how to approach this carefully.

And my advice is not to approach it at all. She doesn’t need your condolences for her recent divorce. Leave her alone.

I'm guessing you are probably under 25yo, so you don't really have much experience with adult relationships. Am I wrong?

Nope. I’m a married 36-year-old with a kid on the way. Try again 😆

Pro tip: if you don’t want actual feedback from strangers on the internet, don’t ask for it. My wife and I both agreed that your post seemed desperate and creepy. Trying your luck with a recently divorced woman is pathetic, period.

And finally, my wife would like to underline the point that you’re not only trying it on with a recently divorced woman, but your OLD FRIEND’S ex-wife. This is a sick mindset, regardless of what he did in the past.

Well I'm glad you got a second opinion from an unbiased source 🙄

I didn’t get a second opinion. We were snuggled up in bed reading the feed together. We mean you no harm, mate. But you obviously knew deep down it was the wrong thing to do, otherwise why would you have asked the internet if you were being a vulture? You deserve to find someone to love and someone that will love you back, but this isn’t the way to go about it.

Ok