lack of food discipline

I have the same issue. Just have to use a lower calorie option to satisfy the urge if it's an everyday thing. Fruit, flavored rice cakes...there are some kettle/caramel popcorn options that are pretty good.

Clio mini frozen yogurt bars. 60 calories, 4g protein. Perfect for the sweet tooth at night.

Evening sweets are killer
My key was to find something that scratched the itch but had a better profile

First it was a small dark chocolate, but only one - that can get out of hand easily

Then it evolved into plain nonfat Greek yogurt with a chocolate-flavored protein powder mixed it. Filling, protein, and curbed the sweet craving.

But every once in a while have to get a real milkshake

You should try being married to a pastry chef.

Good stuff already said.
I’ll add it’s also about total calories for the day so you need to make sure you know what your caloric goals are.. TDEE calculator if needed.
You can ease up throughout the day if you need extra calories at night.

I had the biggest sweet tooth on the planet. A JIF to-go peanut butter cup and a protein shake did the trick for me. It’s 370 total calories but my caloric daily deficit remained and I eventually curbed my sweets craving.

My biggest thing is not sipping on a glass of bourbon. I like to relax while all the kids are in the their rooms and the wife is busy with doctoral school work. So I'm trying to find other shite to occupy my time.....

In skimming the thread it looks like the major stuff has already been hit, but to second some opinions:

1) Prioritize protein throughout the day. Protein is incredibly satiating so you'll find yourself fuller and cravings reduced.

2) Make your evening snack something that is still somewhat sweet but contributes to the protein, like a protein bar, shake, or even a CLIF bar.

3) If you're hitting your protein goals, don't sweat the snacks. I top off my night with a bowl or two of cinnamon toast crunch a few times a week. No big deal, eating right isn't all or nothing.

4) Some people sleep bad like this, but it helps me - carbonated water. Can of spindrift or lacroix in the evening (Maybe cup of decaf is more to your liking) helps to curb my cravings. Particularly booze cravings, but it helps keep me away from the cereal too haha.

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evening sweet tooth

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I do sugar free jello/pudding cup with some sugar free whip on top a couple nights a week

Eta: the Chobani flip greek yorgurts are pretty good if you have a couple more calories to spare

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and hear me out here....stop labeling foods as healthy and unhealthy...make sure you are in a caloric deficit, you have had 1g protein per lbs of bodyweight and you eat what ever you want with the rest of the calories....and get out of the unhealthy habit of labeling foods as healthy and unhealthy....

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To me, this is good advice for people with eating disorders, but not really for the gen pop. Eating garbage will definitely come with negative consequences.