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Different dating attempt and avoiding "friends"


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Over the past year, I've been taking a deep dive into the dating world and met quite a few new and interesting people. These have all been found online or encounters with strangers, but nothing has materialized from it yet. I have not dated anyone in my social circle in a LONG time.


There is an old acquaintance of mine who is also a long time friend of my sister that I am interested in dating. We hadn't known each other well before, never friends nor dated, just knew of each other and spoke on a few random occasions. Prior to recent weeks, I hadn't seen or spoken to her in over three years. We've attended a church event together twice in the last two weeks as a sort of re-introduction, but it wasn't just the two of us nor a setting for flirtation.


We're both older, in our early 30's and at similar life stages. I know she hasn't dated much or been in a serious, long term relationship. She is shy/reserved and has a very traditional approach to dating and relationships as do I.


Despite plenty of recent dating, I'm finding this to be a sensitive and challenging situation. Partly because she's connected to my family but also because I have not been able to determine her interest level from recent but limited contact. I feel that I need to be cautious, but that if I move too slowly it'll become a "just friends" situation. If I move too fast, it could very well become awkward for us with the family connection and seeing each other at church.


She works very close by and I was planning to invite her to lunch tomorrow. We have not had any 1-on-1 time so lunch seemed like a relaxed way to set that up with zero pressure. If we have a good time and I sense some interest then I plan on moving directly to a proper date.


My question is whether the lunch idea is too friendly, not assertive enough and starting down a path in wrong direction. I could throw all caution to the wind and go straight to a dinner date, but think that it may scare her away. Thoughts welcome.

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