You can flirt naturally by telling him how you cute you think his dog is, openly showing affection by petting the dog and asking questions about the breed or age of his furry best friend. This can lead to a conversation about other things and gives you a chance to feel him out and see if there are any sparks between the two of you.
He doesn't have to have a puppy to get the conversation going. If you see an interesting man sitting on a park bench and reading, ask him about the book he's reading, and so on. Keep things casual and cool and you have a low-pressure way to show interest in someone new.
Flirting at the Beach
If you've got plenty of body confidence and a nearby body-of-water, you might want to consider the beach as a pick-up zone. But there's more to it than showing up in a bikini and hoping that a cute guy will happen to trip over your beach towel.
Grab a friend or two and head to the beach for a day of fun. And here's the key: actually have fun! Come armed with some piece of sporting equipment, a cooler full of cold water and snacks, and a great, open attitude.
If a man sees you having fun with your friends - playing Frisbee, paddle ball or sand volleyball - he's more likely to wander over and introduce himself. Likewise, don't be afraid to make the first move. If you see a good-looking man or group of men that are chilling on the sidelines, ask them to join your game.