Confused how the first date went....

We went out to upscale Italian restaurant near my neighborhood. The guy that I’m seeing is the Vice President of Operations for a technology company he owns. He makes a six figure salary (He didn’t tell me, I found out) drives 2 BMW’s and is 35 years old and I’m 26. During the beginning of the date he seemed interested, telling about his career and how his workday went, but then he began to over share about his family problems. He told me his mother is irresponsible with money. She has problems overspending and he ends up bailing her out of financial situations. She always assumes he has extra money because of his career but he says that he uses the money for his investment properties. His father passed away from a motorcycle accident and had an alcohol problem. He said his parents probably divorced because of his mothers spending habits. He said sometimes he gets so stressed he takes Xanax to relax but is not addicted. He said he has a cousin that is addicted to painkillers. He gave his cousin a job to work for his company but he would show up to work high and fall asleep so they fired him.

Then he tells me another story about his other cousin who has connections with strippers. One of the strippers strips with her mother in a strip club and his cousin invited him to tag along with the group in Atlantic City but he declined because he’s not a party guy. He says now that he 35 he doesn’t drink as much as he used to when he was younger and likes to spend most of his time going to sports events, movies etc. he also told me that he’s planning a trip to New Orleans with four of his friends which I thought was a strange place to go to if you’re not much of a drinker, New Orleans is a party scene. I spoke to my friend about everything he said during the date and she said it’s weird that he explained all of his problems on the first date and that he has so many crazy stories. He also asked if I would like to out for drinks even though we had a bottle of wine with our meal which is strange since he’s not much of a drinker and offered to take me bowling. I went home after because I could feel the wine kicking in and had to drive home. He texted the next morning saying he had a good time and hopes I did too but unmatched me on the dating app we met on. He hasn’t said much today either, before the date he texted throughout the day is this a red flag? Also do his stories sound made up? My friend added him on Instagram and his family looks completely normal and they don’t look like they’re struggling or asking him for money.