The small talk at the school gates/ after school activities I find particularly boring. I'm bad at it. Fine in other social situations but that crap just BORES me to tears. No interest to hear how great your child is missus, mines better, get over it ;p
Seriously though, I'm not great at it either but I find if you just keep asking them questions about whatever, they're usually only too delighted to keep talking about themself.
Don't go to parties full of nobs?! Or excuse yourself by saying 'I'm really sorry, but my personal alarm has gone off. I have to go and take my mini-pill now.' Or say 'Yes, but what about the FOOD. Did you listen to my question or are you, in fact, a pompous twat?'
You introduce an innocent topic like "Your favourite food", and the object embarks on "Japanese, in particular, the Nobu restaurant, have you been? it's amazing, the food is great, and, you know, it belongs to De Niro, and there are lots of celebrities there, and I've seen Spice Girls, and it is expensive, they have outlets in Mayfair, and one in Canary Wharf, and all those rich bankers are going..."
Fine, you feel sick within a minute, and you do not want to know anything about this person at all. What to do? Option 1, unproductive, but satisfying, to be an asshole on your own: "That's amazing! How often do you go there?" Option 2, peaceful, but with an unpleasant aftertaste, just smile with random "ah-hum" and run away with the first opportunity.
The problem arises when you are in a quite close non-random company - work colleagues, your club, in-laws convention. How to run away not presenting yourself as a spineless slug, and at the same time stay likable?
Ask questions and give compliments: Did you have a nice weekend? Get up to anything exciting? You always look so smart and stylish, do you have a very exciting job? Things like that. Que them telling you that they did a 30 km triathalon or that they work in advertising and regularly have lynch with bill gates/ olly murs/ dim Helen coronation street actress on I'm a celebrity .......
I find the best way to deal with small talk is to smile and feign an interest in the subject as small talk is often frightfully boring.
Also ensure you can extract yourself from frightful bores. I often find that in that situation I will politely address the group with a smile before saying Please excuse me, I see xxx has arrived/I have to refresh my glass. We will speak again during the evening.
Couple more tips: observe and analyse how other people do it, then copy them. You'll probably feel like a complete lemon the first few times but it'll feel more natural after a while. Have a few pre rehearsed general 'tell me about yourself' questions (where are you from, what do you do etc) and trot them out whenever you can. Ask a follow up question or share some personal info to make a connection. (oh, I've heard good things about Dundee. Do you like it? Have you always lived there? My aunt used to live in Dundee. Etc etc) and just remember, it's actually supposed to be as bland as it sounds
Be boring, banal and brief. Keep it light. It does not have to have any real content. The objective is just to enable the participants to be together and get a feel for whether the other person is someone they might like or, to pass the time in each other's company in an inconsequential way. What is it that you find particularly difficult?