Confusion about Thai Visa-Flights more than 60 days apart

Will I be able to get the tourist visa even though I won't be able to show that I'm leaving the country within 60 days?

You really are confused!

A 60-day tourist visa (TV) is something you apply and pay for BEFORE you arrive in Thailand. It's valid for 60 days once activated, and can be extended for another 30 days for Baht 1,900. You cannot get this visa after you have arrived inThailand, it's not available at the airport, nor at any in-country Immigration office.

won't be able to show that I'm leaving the country within 60 days?

That TV has nothing to do with this. You seem to be talking about a visa-exempt entry stamp. This is NOT a visa, it's an entry stamp, if arriving by air, to allow you stay in Thailand for 30 days, but you are supposed to be able to show proof of onward travel from Thailand before that 30 days period expires. It's never a problem arriving in Bangkok without that proof but it may well be the cause of denied boarding of the flight TO Thailand from USA or Canada. Having a pre-arranged 60 day TV gets you around this requirement.

If you CAN board without TV, then the entry stamp will work for you as you say you will leave Thailand again before the 30 days are up. You get another 30 day stamp every time you arrive by air, but it's only 15 days if you enter overland.

Once you leave after your first visit, get a TV in Cambodia or Vietnam if you plan to stay again in Thailand for longer than 30 days.

If you just plan to enter Thailand twice then by far your easiest solution is just get a double entry TV from a Thai consulate in US or Canada before you leave.

You can also keep heading for the border and leave Thailand, then turn around and come right back in again, as often as you like, but again - if you do this at a land border you'll only get 15 days each time, and it costs visa fees for the country you exit into before doing the u-turn.

Wow thanks for the very helpful response! I have one more question though. Let's say I show up to the airport in Canada and can show them the 60 day Tourist Visa which I will have gotten before the trip. Won't they still ask to prove that I'm leaving Thailand within 60 days? Because my return trip to Canada will be more than 60 days after the first flight. Or will having a TV just exempt me from any questions about the rest of my trip? Thanks again for your help.

Won't they still ask to prove that I'm leaving Thailand within 60 days?

No, they won't ask, so stop worrying about that. They don't care. Their contract is to carry you to Thailand, that is all. You will have a TV to enter Thailand - that means they don't have to worry about the cost of repatriating you if were denied entry. You have a visa already, so the airline is over that hurdle. End of story.

You COULD save money and just buy a single-entry TV, which is cheaper. That gets you on board the flight ex Toronto. Then front up at the immigration desk on arrival Bangkok and smile and ask them NOT to activate your TV but just give you a visa-exempt 30 day entry on the grounds that you'll be leaving again before the 30 days and will use the TV to enter again (but check the date it has to be used by, which is stated on it when you're given it). They usually comply with such a request. If they DO stamp your visa, then you now have further options!!!!!!!!!!!! Either, just fly back in and get another 30 days, overland it for 15, OR get another TV from the Thai consulate in Phnom Penh or Hanoi or Saigon.

Just remember that however you enter Thailand, that entry becomes null and void each time you leave - there is no carry-over of days, or part allowance etc.

I'm a little confused about how the visa situation would work

Understanably so, the visa requirements/allowances for Thailand are pretty quirky.

Having a proper visa in your passport will negate any required proof of onward travel within X number of days. The catch-22 is some Thai consulates in the USA require such proof before they will issue a visa. Check with whatever consulate has jurisdiction in your area.

Or try to come without a visa and enter visa-exempt 30 days by air (15 days by land). That is, if the airline let you go in the first place. Once you've passed airline check-in it's smooth sailing from there.

Read the Thai visa link below for extra info (added confusion)