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@Ali-oop: This all sounds normal!

But I'd suggest getting rid of the underwear and letting him go bare-bottomed to start. Feeling underwear tight against them makes them think they still have a diaper and makes it harder to learn their own cues.

Oh Crap Potty Training is a great resource for what you're looking for. Basically, you start off bare-bottomed and then watch your kid like a hawk so that YOU can learn their cues and help teach them. You're looking for an indication that they are transitioning from Clueless -> I peed! -> I'm peeing! -> I have to pee!! And that's a lot easier without underwear.

Even if they start peeing on the floor and you have to grab them and run them to the potty to finish on the potty, that's a step in the right direction. But you have to be able to SEE what's happening to be able to do that.

Then once they've transitioned to the point where they've peed on the potty a few times, THEN you put on pants (the book suggests you go commando if you can for a while).

It's totally normal for a kid wearing diapers to NOT hold their pee at ALL. They figure it out during the potty training process. And if you have a kid that pees every 30 minutes, that gives you a lot more opportunities for practice, which is helpful!

I agree with @Adira to try bare bottom so they understand fully they are not wearing a diaper/cannot go pee anywhere but potty. I will also suggest that if you keep trying and your LO keeps peeing everywhere, your child might not be ready yet. I tried to start my LO when he was about 2.5 and he just simply wasn't ready and it was too hard. About 3 months later I tried again and it worked. Don't be afraid to say nope, not yet if it's just not working!

I'm with @MrsADS: if you can wait, I would. Probably totally depends on your kid's personality though. O is highly sensitive and hypervigilant, and pushes back big time if she senses any pressure at all (even if it's something she wants to do). I knew the Oh Crap method wasn't for us, so we just casually encouraged potty use as she was interested, and then eventually she stayed dry in her pull up for a few days in a row, so we switched to underwear. She has had plenty of accidents, but never more than 1 per day and probably not more than 10 or 15 TOTAL and she's been in underwear for several months now, maybe 6?

@Ali-oop: He might not be ready. We had some false starts with my son (tried at 2.5 and 3). It wasn't until almost 3.5 that it finally clicked.

We took a slow and steady approach, I know my son's personality and the Oh crap or 3 day methods would have been a disaster. We would do underwear after picking up from daycare to before bath time. I did this for a couple weeks. Then we would do underwear at home but pull ups at daycare (our daycare at the time was not on board with sending in underwear). It took about 2 months but he was day trained by the time we started our new daycare.

ETA: Our pediatrician was very adamant that we not push it. He will train when he is ready.

@Ali-oop: to me, he doesn't sound ready. I would wait a little longer then try again. That really is a lot of pee in a short time!

My older son took a while, we tried, then stopped when he just wasn't into it. Then it wasn't until he was 3.5, we just said, OK, today was the day. Switched to underwear and there were no accidents, it was done. We could tell he was ready to do it.

My younger son basically just said he wanted to do it when he was 2.5 without any prompting (probably because of older bro)... but all that to just say each kid is different obviously. I think pushing it makes it harder on everyone. Take a couple months off and try again

I would probably wait a bit longer as well as some others have suggested. There is a wide range of normal for potty-training and boys often potty-train a bit later than their female counterparts. We tried with no success for DS at 2.5 and then waited a few months (after his 3rd birthday) and it was a different story. I think we tried to push it too soon initially.

@Ali-oop: I agree that it is worth another try. My son turned 3 in July and I was ambivalent about potty training because he was not super interested. But we had the same issue of preschool transition.

We did a couple Saturdays with undies with limited success. Multiple people suggested bare bottom and he didn’t like it. We compromised by using wearing undies as a reward—once he had a couple successful pees on the potty then he could have them. It helped.

We did a modified version of 3 day where we talked it up ahead of time (it was like 2 weeks after his birthday so a lot of “you’re getting too big for diapers...it’s almost time to say bye bye diapers”), and then did cold turkey undies and rewards.

We did a sticker for every try, an m&m for every success and a prize for every 3 successes on the potty chart. There were accidents but he figured it out. He had accidents the first two days at daycare and that was it. This is his second week in the new room and there have been no accidents and he feels so big.

I think he sounds similar to where your son is now so I wanted to encourage you. We never had dry diapers and one of the practice run days he peed on the potty like 11 times (drops!!) to get m&ms.

For me it was that my attitude was going to set the tone and I decided it was time, we would make it fun and positive and get it over with and it worked. I think you could get him trained if you both feel ready to do the work.

One thing that helped me was realizing that "ready" means "ready to learn" it doesn't mean they will automatically do it. It really is a process.