We live close to countryside and my daughter’s first date with her partner was in a very dog friendly pub - although he didn’t bring his dog! I can’t see it’s a big deal, unless she’s not into dogs.
My husband brought his dog to our first date. I didn’t realise until the end of the date, that his dog was waiting patiently in the back of his Land Rover. She jumped out to say hello when we went to leave (obviously, he opened the boot door first!). She was a puppy at the time, about eight months’ old and didn’t want to leave her for the few hours our date would take. I was glad to meet such a friendly dog (Gordon Setter) as I wouldn’t say I was a massive dog person, it it was definitely not weird or anything!