First Attempt - Dismal Failure!

[solideogloria86]

Just checked it 20 minutes ago and the pipe still smells like an ashtray.

Your pipe smelling like an ashtray makes a 100% sense. You've burned tobacco in it and created tobacco ashes.

 

[Sobrbiker]

Pack lighter than you think you should, puff softer than you think you should, tamp lighter than you think you should.

If you wind up not liking it, that’s cool. If you do like it, keep at it and it’ll work itself out. Folks were smoking pipes hundreds of years before the internet and YouTube.

 

[Gimlet]

It's my first experience with tobacco. I suppose my greenness has shone right through.

This is the problem.

Bad (or uncured, not broken in) briar can give you some intensely bitter and acrid puffs. Black cavendish is your friend here, just smoke a bunch of bowls that are overly sweet until that pipe settles down.

You may want to add a filtered cobb for comparison.

And this the solution. I'd definitely start with a filtered pipe. I'm a returning smoker. I smoked a pipe 30 years ago, went back to cigarettes, then quit those for 17 years before taking up a pipe again as a hobby and a pleasure rather than an alternative nicotine source, as I was no longer addicted to nicotine.

I've now got both filtered and unfiltered pipes. I've smoked both side-by-side and I greatly prefer the filtered. They take a lot of that ashtray taste out by removing excess steam and tar and cooling the smoke and allow me to just enjoy the flavour and bowl scent.

I'd say, go and buy a decent mid-priced 9 mm filter pipe. You'll get one under £50 but avoid the dirt cheap "beginner" pipes. I started with a £100 Barling Marylebone, which turned out to be inspired because it's very easy top smoke, require very little breaking in and seems to suit most tobacco styles.

Don't get anything with too big or too deep a bowl as they are trickier to pack consistently, maybe a medium sized apple, billiard or bulldog shape. A longer stem will help deliver a cooler smoke. bent stems smoke cooler than straight stem (IMO..) but can gurgle more easily, so maybe start with a semi-bent.
Something like this would probably be a good start-up pipe:

Rattrays Mary Grey 161 Fishtail 9mm Pipe (RA1377)

www.turmeaus.co.uk

And use good filters. Vauen Dr Pearl are the best I've found and the most widely available. By all means try a filtered meershaum cob, even if the style doesn't appeal, because they're very novice-friendly and very cheap to buy.

And be wary of English blend tobaccos that contain Latakia. It's a love-hate tobacco. It has an intensely smoky, tarry, peaty flavour. And it will taint (ghost) your pipe forever.
Plain blends with burleys, dark virginias (rather than hot and bright) and black cavendish are neutral and "tobacco-y", without strident artificial flavourings. Petersons Elizabethan mixture, Irish cask and Luxury blend are all good. As are some of the Century and Gawith Hoggarth American blends, like black Cordial and American black and brown.

You can build from there and discover the flavours that appeal while learning to get the best from your pipe.