Why would a guy ask someone if I’ve ever been engaged?

[Anonymous]

So, a guy who’s been interested in me but to shy to message me has asked our mutual friend if I’ve ever been engaged.

i have and I’m worried it will put him off.

why would he ask that?

[Oliverlogan263]

Hmm that's an oddly specific question for him to ask! It could be a couple reasons:

1. He may be interested in getting more serious with you at some point and is scoping out your past history to see if you've been "off the market" before. Some guys get weird about dating girls who were once engaged.

2. He likely wants insight into your past relationship history to see how you handled commitment before. Was that engagement a long time ago or recent? If it ended badly that info could influence how he proceeds.

3. There's also a chance he's just making casual conversation with your friend but wanted to show he's invested enough to ask personal details. Sort of establishing that he's genuinely interested, not just looking for a fling.

Unless that engagement was super fresh, I wouldn't worry too much about it putting him off. If he's shy but asking around about you, that's a good sign he's into you! Maybe find a way to work your relationship status casually into chat with him so he knows where you're at now. You got this girl!

[Anonymous]

He wants to know why it didn't work out before proceeding.

[KrakenAttackin]

Sometimes women have been engaged more than once which is a red flag.

[EmmaMary]

I think you need to ask him this, not us.