If you spot a girl you’re interested in & it’s peak hours at the coffee shop, just ask her if you can sit by her table since it’s packed or just sit down at the table next to her if there is an open spot & after getting settled in just ask her if she knows what the Wi-Fi password is, if she’s got an iPhone charger, or ask her what she recommends if it’s not a Starbucks or a chain. Just be mindful, if she doesn’t look stressed, completely consumed with whatever she’s doing, or is on the phone get creative & immediately segue & ask her what she’s doing (blogging, reading, studying, thinking, etc.)
Know when to end the conversation. Going on for too long can make you seem desperate or even scheming. When this woman is someone you'd really like to see again, say something like, "You know, I would love to hear more but I have to get back to work now. Tell me all about it over salsa dancing on Tuesday." Always leave the conversation to be continued. Do not exhaust the conversation as things can turn awkward and she may lose interest.
Public transportation can be one of the hardest places to strike up a conversation with a girl but, also incredibly rewarding if it goes well. It’s quite ironic because you could be sitting next to a girl for the next hour on the bus or train during rush hour. There are plenty of opportunities to chat a girl up but the most important this is to be mindful of her emotions, space, & comfort. It’s very easy to come off as a creepy guy if you’re not aware of these things
When I worked downtown, I made it a habit to eat at all the local hipster places for lunch. Sure, it wasn’t always cheap however, I noticed an upside to it (aside from the often great food). A lot of women were doing the exact same thing as I was. They’d sit down next to me and we’d strike up a conversation. Yes, women eat alone too! Although, these weren’t always just women that worked nearby. The truth is, a fair number were from out of town, and quite lonely while looking for companionship in the city.
Yes-older woman run to stay in shape just like you do, especially older women seeking younger men. After you have established your jogging routine look for familiar faces as you run. Jog alongside and make casual conservation-about anything! The scenery, the length of the run..anything to get her talking to you. Try to be in the same area at the same time each day. You want to make it look like this is something you do every day (you should anyway) so she doesn't think you are stalking her!
Be open-minded to all those interested in you. If you put an age-range or any other restrictive ranges into your wishlist, you could miss out on women who might be slightly outside those expectations but are ideal for you. It also sounds really bossy and perfectionist to list restrictive preferences and will scare off many women even if they fall within your restrictions.