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Ok firstly, I have a 1.5 year old Black Pug (Doug), whom I got from a fabulous breeder, He is very well trained BUT quite hyper and is used to playing with big dogs (as he thinks hes a great dane)

I just recently Introduced a new rescue (Pug Boston X, Skeeter) into the house, and they've been doing great, no jealousy yet as Doug is not alpha at all, and the attention has been divided. Skeeter is 8mn and previously sat in an aquarium, in his own filth, for 5 months.

He currently has a UTI because of this, but has a great energy level, anyhow the QUESTIONS:

1. Doug & Skeeter love to play, which is awesome because skeet needs to lose 4lbs before I neuter him, BUT his skin etc is so so sensitive (I believe from never being outside/exposed to ANYTHING) I believe Doug is playing a little to rough as hes used to playing with Golden Retriever Puppies, How do I teach him that he needs to be a little gentler with skeeter, at least for now??

2. Skeets has a UTI :( Hes been doing awesome at going outside to pee, and waiting at door etc, but hes left alone for about 5 hours in kennel at night and Pees during this time. I know some of it is the UTI but Also because hes used to peeing on himself whenever , when he was elsewhere. Tips on how to break this habit ?? Or should I wait and see if it goes away with the UTI ?

3. This is more so curiosity - He is TERRIFIED of older men !! (but fine with young men, I believe he was hit by his previous owner, but the younger men in the workplace where fine) My father is helping me take care of him and we're going slow .... any tips to have him warm up faster?
 

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I probably wouldn't have high expectations of potty training until the UTI has cleared up. The poor guy may not be able to help it at all. You might try setting an alarm and getting up with him in the night like a puppy.

I'd have your Dad feed Skeets and give him treats so that he can start seeing that good things come from older men. Even if your dad can only come close enough to toss a treat without frightening him, it's a start.
 

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Welcome!
As for your questions:
1. Does Skeeter yelp or growl or respond in any way when Doug is too rough? Usually, one dog will let the other know. If Skeeter makes a noise, and Doug responds by stopping for even a second, I would praise him, and maybe offer a reward of some kind. You can even give it a name. We call it "gentle" and use it for when our dogs are playing with the cats and need to not be so rought. So, we say "gentle" and if the dogs respond we say "good gentle!" and maybe a quick cuddle or some praise. Also, you might up Doug's exercise and free play time right now, so that he gets more opportunities to expend that energy besides on Skeeter.

2. For the time being, I would set an alarm during the night and take Skeeter out to pee. Even if it's because of the UTI, it's still a good idea to prevent him from peeing in the crate, especially since he kind of already has the idea that it's ok to pee in the crate (due to his previous life).

3. Rather than having your dad actually offer or hand feed Skeeter a treat, have him toss treats in Skeeter's general direction. That way, Skeeter can enjoy the treats, without having to be afraid to come close enough to actually take them. Then, over a bit of time, he may feel comfortable enough to actually get close enough to take them from his hand. But, for now, whenever your dad comes into the room, have him toss the treats towards Skeeter. When he passes by Skeeter, same thing. If the treats are yummy and there's no forced interaction, he may build up a positive association with your dad.
 
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