It took me until my 20s before I could swallow pills without gagging and spitting out water.
Then one day something just clicked and since then, no problem.
I can do one, two or even eight at a time like it's nothing.

When I got married and had a kid, I discovered "trouble swalling pills" is indeed a phenomenon.

I have been taking pills since I was five thanks to my temperature-based allergy. I just salivate when I see a pill. It's quite inconvenient when I am handling my child or spouse's medicine.

As a kid? Yes. I have a very strong gag reflex. The doctor using a tongue depressor would make me retch. I had trouble swallowing meat if it was tough or fatty. I would have to chew it for a very long time before I could swallow it. Fatty bacon I usually just had to give up and spit out.

It took me until I was a teenager until I could swallow a pill. I practiced on swallowing blueberries.

Now I have no problems, I can swallow a handful of pills and I'm a vegetarian.

Tilting your head down can actually help with swallowing by a lot.

Insert pill. Put liquid in mouth. Tilt chin down. Swallow.

Source: have dysphagia, can only swallow pills and other hard substances by tilting head down

I've been taking 6+ pills a day for years and still can't get myself to swallow them. I just chew everything. Tasty painkillers and caffeine.

Someone already said it, but tilting your chin down opens your throat, while tilting your head back will constrict

Tucking your chin down while swallowing pills is best

For me it’s the size. Can not really trick my body to just swallow. „But that’s huge! We have to chomp on it to break it down! Trying to kill yourself by choking?“

I'm a 34 y/o man and I need tricks to swallow pills. It has nothing to do with taste at all, it's about capability. I actually have a condition that makes it difficult to swallow.

It’s soo ridiculous the hoops a person would go through to avoid a slight bitter taste.

I figured out a fix for the avoidance of horrible tasting medicine:

The simplest and easiest way to use it is with an ice cube or two. Get the pill/liquid medicine you have to get down your throat ready, your ice cubes, a cup of water and stand in front of a sink. Put the ice in your mouth and let it sit on your tongue for 15 to 60 seconds. Yes, its going to be cold and slightly uncomfortable. The longer you can stand it the better your result. After this time has passed with the ice in your mouth your tongue will be numb. Spit out the ice in the sink, you'll have 5-15 seconds where you can't taste a goddamn thing which is plenty of time. At this point you could put the most disgusting flavored thing (sour, bitter, etc) and you won't be able to taste it. Quickly get the medicine in your mouth and chug that full glass of water. Taste will start to return within about 3 or 5 seconds of chugging water, so make sure you drink enough to clear your mouth of whatever bad flavor you're trying to avoid.

This whole process adds perhaps 2 minutes tops to taking medicine. For those that have difficulty this is a tiny fraction of time usually spent avoiding taking it, or the recovery process for taking it normally.

If you need more incentive (especially for kids) instead of using ice cubes and spitting that out. You can use ice cream or milk shakes and just swallow those. Same rules apply: put the ice cream in your mouth and let it sit on your tongue as long as its frozen. Its a little more involved than ice cubes because you might have to have two or three spoonfuls to get your tongue numb.

If they'll hold the pill in their mouth... Mine will spit if it is even a tiny bit sour or bitter.

Aren't there slow-release pills that shouldn't be crushed?

As a kid the bitterness of the crushed pill made me gag, even when mixed in something sweet like jam. Maybe my folks just needed to dilute it more with like an entire bowl of ice cream or something but I remember throwing up more than once because of the disgusting taste.

By the way if anyone's curious yes you can crush up Viagra, put it in Vaseline, and use it as a cream.

Yes you can put it there, and yes it's effective.

I've done it multiple times for people that would regularly go over that five hour limit, because skin absorption is slower and weaker than intestinal absorption.

I don't think it works on cats :(

Why would you do one pill at a time? Just put em all in and wash the pills down with a glass of water.

I can't swallow pills without water. They get stuck in the back of my throat.