If you’re a physically active person or you’re trying to get back into shape what better way than to kill two birds with one stone than join a workout group, a co-ed sports league, or maybe even a running club if you’re into running. The beauty about joining these clubs besides finding like minded people (if you’re a workout warrior or love being physically active), having accountability, & a fun way to get into shape is that it helps you expand your social circle & these classes are usually heavily populated with fit & attractive women looking to break a sweat & socialize. I’d also like to add from my own personal experience is that because of the accountability & support system you’re more likely to stay with your fitness goals since you’re doing it with other people who are going through the same thing as you & you’re never bored.
Do you have a dog? If not, get one, or borrow one from a friend. Offer to take the critter for a walk around town or in the park! Mature women love to see a young guy walking his pet and she might strike up a conversation with you-especially if she has a dog of her own. If it happens to be a younger woman who tries to come on to you, be polite but move on.
Get to know them, learn their names, and remember them! Make it a point to recall what drinks they like to order or foods they like to eat, and of course, flirt a little! Just don't go overboard. A little mystery is fascinating to any mature woman, but especially so for an older one. Flattery is one of your best friends-and believe me-older women will remember it long after they leave. They (or she) will undoubtedly know what you are doing and will love it!
For some strange reason especially when I’m doing my grocery shopping and running errands I’ve always managed to meet the prettiest women at the local Whole Foods. It’s really easy to come off as creepy if you’re trying to chat up the pretty brunette you saw at the frozen food section so the best tip I can offer for you is stay away from using weird innuendos & puns involving melons, bananas, & other foods shaped like sexual organs. The best time to socialize with a girl at the local grocery store is while you’re in the checkout line or you’re waiting in line for a fresh cut of meat or fish. If however there aren’t any women in line & you manage to see a girl that’s really caught your eye, I’d recommend chatting a girl up at the food court section since a lot of Trader Joe’s, Whole Foods, & even Costco have large food courts.
For short-term relationships and sex, you may want to look for someone during your night life—particularly at bars, clubs, and restaurants. Individuals at such venues may be more likely to have similar short-term and sexual goals as well. Also, bars and clubs may offer a better chance of getting noticed, flirting, and touching to build sexual attraction. Such meetings may still require self-introduction though. Therefore, you may have to overcome anxiety, learn to break the ice, and ask for what you want to begin an interaction. In this case, however, a bold pick-up attempt and being direct with your interest may help increase your chances of finding a like-minded lover.
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.
Read the signals: A woman’s body language is a good way to determine her interest. Is she leaning towards you or are her arms crossed? Is she asking you questions or simply being polite? Is she playing with her hair or fidgeting to try to get out the situation? Follow her lead to ensure that you’re both going in the same direction. If she is not encouraging your interest, take a step back and let her be.
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.