Cocktails, the libationary art!

And my wife loves smokey drinks so it’s way up high on her list as well.

Adding a small update based on this: Maybe she'll like a Homely Smoke.

I definitely recommend a second try at an Old Fashioned, our tastes seem to have quite a bit of overlap and it's by far the drink I make the most - just start with the the IBA recipe since most you find around the web add way too much sugar. Also, you may want to test different types of whisky, I prefer mine with Scotch instead of Bourbon, and I also suggest adding a couple drops of Orange Bitters if you have them.

Since you mentioned Sazerac I imagine you already have some Absinthe, so maybe try a Monkey Gland? It's by far my favorite Gin drink, the balance between sweet (from the Grenadine) and sour/herbal (from the Absinthe) is fantastic.

A friend of mine who is a huge fan of Negroni also loves the Teresa. It's an interesting one to taste since it feels very sweet at first due to the Cassis... but then the Campari hits and overpowers that with its sour flavor.

My favourite these days is a paper plane.

Go with small variations on what you already like. You like negronis? Try a boulevardier (gin -> whiskey). Other swaps exist for just about every classic cocktail.

Separate recommendation is to follow the learning curve of the book "raising the bar". It's fantastic and really did a good job of teaching the fundamentals with as few bottles as possible.

For something completely different. Try a Paloma. Perfect spring or summer drink. Get a good mezcal.

I second the boulevardier mention. The paper plane has also become a mainstay in our house.

Def on the sweet side of things, but as an ex Mormon, why not combine alcohol and coffee! Try espresso martini :). Shot (1 oz) espresso, 1.5oz vodka, 1oz Kahlua, .5oz simple syrup. Shake with ice and strain into martini glass.

In the Tequila corner:

Margaritas with no sweetener, just 2 parts tequila, one of lime, and one of orange liqueur, shaken.

Siesta, again with no sweetener - 2 parts tequila, 1/2 part Campari, 1/2 part lime, 1/2 part grapefruit, shaken then express a grapefruit peel over it.

Oh, also congratulations on your recovery from Mormonism and my penultimate daughter asks what is your fastest time solving the basic Rubik's Cube?

As others have said try a Boulevardier.

You like a Manhattan so try these variations to see what directions you like.

Rob Roy uses scotch as the whisky.

Martinez the missing link between the Manhattan and Martini. Uses gin and SRV (sweet red vermouth)

Black Manhattan is my favorite replace half the SRV with Amaro. I recommend Cynar as the Amaro.

Any drink using SRV can be made black by replacing half the SRV with Amaro.

It uses Mezcal not Tequila but a Dead Lady is a great drink.

Mezcal and Cynar play very nice together. The Cynar brings out the grassy flavor in the Mezcal.

One of my favorites: A jack rose.

1.5 oz applejack .75 oz lemon or lime juice (I like a 50/50 mix) .5 oz grenadine (real pomegranate syrup if you can find or make it)

Shake, double strain, serve up, garnish with lemon twist.

My standard cocktail at home is a Tommy’s Margarita, sometimes with some added mezcal. Great if you like sours, like whiskey sour.

My proportions: (1,2,4) 1.5cl agave syrup 3cl fresh lime juice 6cl tequila (I prefer tequila reposado)

Shake well with ice. Serve with or without ice.

Don’t buy shitty tequila but it doesn’t have to be fancy. Should always be 100% agave, from Mexico, and never wear a hat.

And like I said, sometimes I do half and half with tequila and mezcal, so 3cl each. Mezcal is basically tequila, but the agave has been smoked under ground, which adds some nice smoky bites.

Try a Twice Up if you haven't. 1 part whisky, 1 part still water, ice optional. Works great with most aged spirits IME.

I don't usually like bitter drinks, but I love Fernet and there's a ton of great stuff you can do with it. The Toronto cocktail is pretty obvious, but it also mixes great with coffee liqueur and even coffee, which has the benefit of giving you control over how sweet the drink is. It also makes an interesting variant of a Black Manhattan.

They're probably out of fashion for fancy cocktail bars but I'm fond of a Japanese slipper - equal parts Midori (melon liquer) / Cointreau (triple sec) / lemon juice (0.0%abv margharita mix goes okay) over ice. Sweet and sour.

Mojito is another nice lighter drink, mostly soda water, then rum, lime, sugar syrup and mint.

Congrats on the journey! This is something I've been enjoying lately, but it sounds like it might be too sweet. I'm still trying to find the balance that works for me.

2 oz. Canadian Whisky 1 oz. Dry orange liqueur (I use Pierre Ferrand) 0.25 oz maraschino liqueur 1 oz. lemon juice

Try a classic gimlet and if you like elderflower, add a half oz to an oz of St. Germaine's to take it to another level.

Edit: make sure you shake with ice and pour neat! It makes a huge difference in texture.

Water on the rocks. Nothing quite as refreshing.