At what point should I start getting pissed? UPDATE IN OP

I don't understand who you are pissed at? Yourself?? You made a dumbass choice. Own it already. You have nobody to pissed at but you for making decisions that if anyone else on the board would've posted about, you would've ripped them a new one.

There is the old addage that if a man wants you, they will move heaven and earth to be with you. In my life this has turned out to be true. All my ex-boyfriends that I chased are ex's and the one that persued me is now my husband. Let him chase you, if he wants to be with you, he will.

This was true for me as well.

I only read the first three pages. There is a chance he is just using you/not that into you

Or, more likely

Based on what he has said, he is ADD/ADHD. I have some ADD tendencies and my one son has pretty severe ADHD. This is par for the course. People with ADD can be lovely, clever, fun, friendly, intelligent and even fairly or really successful people. They can also be procrasinating masters. He will need reminders because his brain is all over the place and he probably has twenty different things he is also into/doing right now. If he has ADHD he also has impulse control issues and might bite off more than he can chew. He means well. He isn't being an asshole, he struggles with organizing and prioritizing shit. You have to decide if you can deal with this.

Even the planning the dream trip while not taking care of the practical is sooooooo very ADD. I know.

If I'm right, he will do what he needs to do--at the last minute and you'll have a lot of fun on the trip together. You will need to decide what you can work with. Unless he gets behavioral/cognitive therapy and/or medication, you will continue dealing with this in the long run.

I'm a little disappointed that so many refupeas kinda gave Yubon such a hand slap.

Sometimes even level headed strong women let their guard down & lose focus. I think she was looking for a little support along with a bit of a butt kick with this situation.

Yubon, you let your heart lead your head & now you must pick up & move on. If he shows up, enjoy it. If not, enjoy the trip & let it go. Don't beat yourself up. We all make a decision that might not have been the best choice on occasion.

I'm still wrapping my brain around the fact that $1800 is no big deal.

You might ask him directly if he thinks he has ADD tendencies. He didn't become successful by not having overcome difficulties. If he has an attention problem, he'll know it.

If he does, then you can learn what comes easily for him and what is a struggle.

You might be surprised. It might work out great. Sounds like you're really good at planning out details. Great! You can plan out detailed stuff! Plan away to your heart's desire!

He'll be the one to grab you and tell you to come right this minute to see a spectacular sunset and teach you to appreciate the moment.

Stranger things have happened. 

ETA - simple answer here is to get his assistant to file the paperwork or sit on him until it's done.

My last 3 years totally validate this post. I've pretty much lost my business over it.

Ok- I've only read through page 5 on my phone, but here are my thoughts...

I would be getting pissed now. BUT... we don't know or fully understand your relationship with this guy that lives so far away. 8 weeks is still plenty of time to get a renewal. Everyone needs reminders in life, so maybe give him a couple more, like he asked. But step back and truly listen to his response each time and see if there are flags raised. Listen to them like you would if it was another Pea telling this story.

Now- that nice stuff being said, here's a story for you...

I have also known someone since high school in the early 90s. I'm in Iowa, he is in Tampa, Florida. Through Facebook we started becoming friends again (not anything romantic on my side, his side yes and I did shut it down after I realized his scam). Anyway, just normal "what ya been up to" kinds of conversations. Life, marriage, divorce, kids, etc. eventually he started telling me how well off he was, kept always just trying to make himself look amazing. Always traveling here and there, and never posting any photos or anything. So I asked him to send me pictures of him and his sister at the beach (he supposedly went to SoCal with her). He wouldn't share pictures or even just text me one... just small things like this that didn't add up. Or I'd remember things he said and then later some little detail didn't make sense. So, I did a Google search.... and whammo! Seriously I found mug shots of him. Without a bunch of details, this was obviously a red flag. I called him out on things and that was it. He still tries years after to be friendly with me, but I know my boundaries and he isn't crossing them. To my knowledge I'm the only person who knows about his true existence, and he can trust me so far to keep it secret with him. But if he crosses a line or treats other people poorly, he knows I'll tell his story.

Obviously I hope something like this isn't going on for you, but it's a reminder that online and long distance friendships aren't always what they seem.

Go on your trip with ZERO expectations of him or a future, and you will have a good time with your friend and DS. If you have ANY expectations, you will likely be let down.