Recently got back in contact with a woman that I really like. How do I gear up from casual conversation into telling her that I have feelings for her?

[Anonymous]

I met this woman on Instagram - we're both Voice Actors and we had a really good bond. I developed a crush on her but I didn't do anything about it and we drifted apart. After a couple of years, I recently reached out to her as a 'Hey, how are you?' kind of thing and just asked her how life and work was going. We've exchanged a few messages that have been light and friendly but I really like her and want there to be something more but I have no idea how she feels about it. I don't want to just dive in head-first and completely ruin everything but at the same time, I don't want to sit back and let a big chance go by. Also, we live in different countries and it would be long-distance if anything came of it so that adds quite a big barrier to it.

How can I take it up a notch and let her know that I like her without overdoing it?

[DaveJord]

You don't tell her you have feelings for her, you keep it casual and work it into a date and you just start dating again. Do not confess your feelings to her, before you start dating her.

Sure, at some point down the line you tell you how you feel but not too soon or too early.

[Anonymous]

Instagram + messaging + long distance = one big fail.

Don't waste your time.

[Asker]

Ok, fair enough.

[WanderingLoveWizard]

Ask her if she wants to be penpals with benefits