Ex Borrowed Money, Do I have a case for Small Claims?

Location: Indiana, USA

Hello, I (27M) came out of a relationship around mid-April that started early December 2024 and my ex (26F) repeatedly borrowed money from me throughout the relationship, totaling in around $2000. This was for everything she needed while we were on trips together, ranging from groceries to hotels to her pet’s vet visit.
She has been unemployed for about a year since the beginning of the relationship, getting by with money handed down to her from her late grandfather, managed and sent to her by her aunt every month. She verbally agreed multiple time to pay me back over time with money from her allowance, but every time I mentioned money, she would shut down and refuse to talk about it. She also never confirmed that she would pay me back over text, so I can’t “prove” that she agreed to pay me back for everything.

We eventually broke up (unrelated to money issues). A few weeks ago, I reached out to get some closure on the relationship, which she responded to relatively quickly. However, as soon as money was brought up, she no longer responded to any of my messages despite me reaching out for a response multiple times. At this point, I just want to file a case for small claims, but I want to make sure I have a case before moving forward.

Reasons for why I believe I can build a case in small claims court:

1. Receipts/card transactions for all of the purchases I want to be reimbursed for, along with chatlogs that proved we went to those places
2. Chatlogs of her responding to messages pertaining to the relationship, but ignoring anything involving money
3. Chatlogs that can be used to build a character profile of someone who had no intention of repaying borrowed money (fiscally irresponsible, going to concerts despite owing money, profile active on dating apps 3 days after our breakup)

Reasons for why I may not have a case:

1. She never acknowledged paying back money in chat logs, only verbally
2. I never pushed for her to start paying me back until we were nearing the end of the relationship, which was also done verbally in call. I allude to it in chat, but she never acknowledged it in the chat logs (“I’m sorry if it felt like I put you in a corner”), which she might use to reason I didn’t care about being repaid or something

Please let me know if this sounds like something I can pursue, or have to eat the financial loss. I’m currently struggling with student loans and in need of a replacement car, so I really want this money if I can fight for it.

TLDR: My ex verbally agreed to repay me for things I paid for her (Hotels, groceries, etc), for about $2000 worth of things. She hasn’t paid me back, but I don’t have any messages of her acknowledging the agreement. Can I build a case in Small Claims court using receipts and chatlogs that show her character as a person?