How do I progress from friends to a more serious relationship over text without being too bold and obvious?

Anonymous

Backstory... so I first met this girl years and years ago when she spent a few months in my class at school. She’s super cute and I had a massive crush on her, but I never really got to know her in person because she was quiet and conservative, and I was too shy to talk to her properly. However, after she moved out and left my class, I occasionally contacted her over text for a little catchup.

These occasional catchups would only happen about once every few months and went on for a few years, but it was just as distant friends and nothing else. It also seemed to mostly be one-sided and every time she'd always start off really outgoing and interested but would fade out and dead it. It never lasted more than a week or 2 and regardless of who started the conversation, she was almost always the one to end it. Then after a year of no contact at all, she messages me out of the blue and suddenly she’s way more friendly and outgoing than usual and this time we’re both evenly contributing to keeping the conversation alive.

We’ve now been messaging every day for the past 5 weeks and everything’s going well, but I want to know how to slowly progress this relationship into something more serious than just friends. As I said earlier tho, she’s super conservative and I don’t know for sure if she even likes me as anything more than a friend, so I feel like doing anything too bold or sudden would put her off and end it.

How can I slowly and subtly let her know of my true feelings for her? And what can I do to try and make her like me in a more serious way? I want to try and test the waters to see if she shares the same feelings toward me before I launch into something that I can’t back out of. If she has feelings for me that’d be amazing, but if not, then I don’t want to screw up whatever our current relationship is because she’s still a cool fun person to chat with.

Also, she’s like a solid 8.5/10 and I feel like she’s definitely out of my league XD

How do I progress from friends to a more serious relationship over text without being too bold and obvious?
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