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!
A quick tip: a great time to chat people up is when you’re in line for the show or at the concession stand before the show starts, I wouldn’t recommend trying to talk to a girl you’re interested in during the middle of the show. If it’s a show where people are dancing, if you took my advice by taking dance classes this is where it would come in handy. Don’t forget to have fun & just please be mindful & don’t try to grind on her or be the creepy guy who grinds on women from behind.
A little unconventional but I can attest that speed dating is a fun alternative to meeting people & meeting women at a very high volume in the shortest amount of time. The best part is if it doesn’t work out or you just don’t click with whoever you’re matched with you’re immediately matched with another person. Speed dating events usually provide questionnaires & surveys for you to fill out to match you with people who have similar interests & traits. If you don’t like structure & love spontaneity I’d recommend just trying it out & socializing with as many women as possible even if they’re not in your cohort. I can tell you from experience most of the dates I’ve gotten we’re girls I talked to before the event in the lounge area & the funniest part is I was never matched with them during the actual event. If you live in the NY metro area check out the following links:
Daily places where conversations might be possible with women include the laundromat, waiting at a bus stop, shopping (including saying hi to the shop assistant you fancy so much), working out at the gym, walking your dog, clearing up your front yard as she passes by, the library, the video store (you already know her taste in movies), large outdoor events and pursuing recreational/sporting activities.