It is VERY HARD to talk to people for the first time and then ask them out in the same conversation. It might be easier if you join some sort of social group where you can 1) meet lots of new people, and 2) see the same people on a regular basis. Then you can have friendly, low-pressure conversations with people and meet them gradually. If you meet a woman and hit it off in this context, you will already be acquainted by this point. And you will have a pretty good idea of whether she likes you back.

Meetup groups are great for this, especially if you go consistently. If you know you will probably see someone next week, there’s not so much pressure to ask her out this week. Intramural sports, walking groups, cooking classes, and basically any other community event would work well.

As far as your second part, our generation got pretty messed up by the recession, and a lot of people in their late 20s are still struggling. I know a lot of people who manage to date successfully in spite of this. It makes a huge difference if you have a self-sufficient attitude about things. Like, are you willing to take the bus or find ways to get around? Or do you need rides everywhere? It also makes a big difference if you have goals and plans, vs. just lounging around at this stage of life. I think as long as you have an independent attitude and a desire to improve yourself, you will be able to find someone. Women these days aren’t gold diggers, they just don’t want to date a couch potato.

Great advice, @Haleth! Your post should be printed and framed. I think that how you treat women is more important than how much money you have.

@Haleth That was really nice. I really appreciate your response and feedback. It helps a whole lot. I am working at the moment, and hoping to find a higher paying one soon. Thinking about going back for my Masters as well. I love Football (Soccer), so a good Intramural league would be a nice way to meet women. Thank you.

@2davidc8 Thanks for the response. I really appreciate it. Some times it depends on the women as well. Some would rather be with a bad guy with lots of money than a good guy who is a work in progress. I completely agree with your statement. Thank you.