How do I paint an outdated ordinary wooden dining room set.....?

As some other people have said, you pretty much have to do a little sanding so the paint will be able to stick. You don't have to remove all of the existing finish, just roughen the surface. I would use 150 or 220-grit sandpaper. Go over the surface just enough so that it doesn't have any shine left. It won't take very long... don't worry.

Next, and very importantly, APPLY PRIMER! The primer is designed to stick like crazy and will enable the paint to stick to the furniture. Without it, the paint will peel right off in no time. "Kilz" is the brand that's common around here, but any latex-based primer from a hardware store should do. It's available in cans or spray-on.

Next... paint! I'd recomment a good quality, semi-gloss (medium-shine) latex paint for durability*. Also use a quality brush to avoid ending up with bristle marks that will detract from your finished project.

(*Oil-based would be even more durable than latex, but it's much nastier and harder to work with, so I'd avoid it.)

Bad News..LOL But if you want the paint to adhere, I don't think there is any way to get around some sanding. I hate it too:) Especially your table top though, will HAVE to be sanded. If you have an electric sander, it shouldn't take too long though. Then make sure you put on several coats of poly for protection, or you'll be in trouble in no time. Just lightly sand the chairs by hand, as long as you just get some of the old finish off, they should be o.k., as long as the paint has a "little tooth" to hold on to:) You might try checking around at some second hand/thrift stores for a new set if you are just tired of your old one, then sell it, and save yourself all the hassel:) I've found a lot of great deals on craigslist.org You just type in the city nearest you, and that way you don't have to worry about shipping, etc.

Good Luck!!

A little sanding would really help the paint to stick, especially on the table top where you want it to be durable. Just enough to rough it up is all you need. There is a product that removes gloss - called Gloss Remover or something obvious - that you can get where they sell paint, but I don't think it is really as good as sanding. Try that if you really hate to sand and use a primer and good luck!

An antique white would look lovely. You are correct on your procedures as to how to paint it. Sand real well first and use a Kilz Primer and then sand lightly "again". Kilz Primer is used on Wood and SheetRock alot because it will cover any imperfections and Stains that may be on the Surface. You can buy refinishing Kits for your Dining Room Furniture at Lowes. I used a Crackle Finish on mine and it turned out Lovely. If you do not want alot of shine on your Table, stick with the Semi-Gloss Finish.

the hardware store has a product that peals off old finish. you could consult somebody there and learn the possibilities.

Sell it and buy yourself new furniture. Painted furniture looks like crap in no time.