I've known for years my hearing isn't great, but it was the most noticeable it ever had been on a recent business trip. In loud settings like bars, restaurants, or stadiums I have to ask people to repeat themselves way too often.

Obviously I want something discreet, just don't know all that much about the process to getting hearing aids, best options for minimal disruption, etc. likely something I would only use for social situations.

Any tips or advice appreciated, especially from the 30 and 40-somethings. Thanks

A buddy of mine in his early 40s has these. I can never tell when he's wearing them. He's been super happy

https://www.starkey.com/hearing-aids/genesis-artificial-intelligence-hearing-aids

Not hearing aids but I was having a similar problem at my daughter's volleyball games.
I bought some Vibes High-Fidelity Earplugs and they make a huge difference. I've worn them in concerts and bars too and they help me hear much better above all the background noise.

Two comments:

The Phonak Sphere Infinio is currently generally recognized as the industry leader for speech-in-noise performance - the issue you described. They're not cheap but they have leading edge technology and outstanding reviews.

Learn about Real Ear Measurement and ask your audiologist if they use it. The process is key to optimizing the fine tuning of hearing aids for your specific needs.

Both true statements

I feel like I go through seasons like this as in some parts of the year I really seem to notice that I'm either having people repeat something they have said or I just don't catch it, especially in restaurants and events.

I've wondered if it is seasonal and related to either allergies or a really heavy amount of ear wax. I don't know if either of those could make that much difference, but I don't have a great explanation for why it not fully hearing people isn't always an issue.

I had a pastor who also taught woodworking and hadn't worn ear protection adequately. In his early 50s (or late 40s) he finally got hearing aids. He regretted not getting them early and hadn't realized what an impact not being able to having meaningful conversations in public places.