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Best to stay away from dating people you see regularly?

The last 2 girls I dated came from different friend groups. One of them was from band, and I befriended all her roommates. It got to the point where her roommates liked me better than her, and one day one of them came up to me and told me that she had started cheating on me, I was 'too nice a guy' to deserve her. Unfortunately because of how that played out I still can no longer hang out with them because she doesn't want to see me ever again. Evidently telling the guy she was cheating on me with what happened goes 'too far'.

Or the last girl I dated came from a good friend of mine introducing us to a close friend of his. She started spending a lot of time with our group, and we hit things off well. We dated for 4 months until she broke things off and said she wanted to be 'just friends'... then couldn't stick to her own agreement and tried to be friends with benefits even though I still cared for her. After a month of her trying to hook up with me I told her I could no longer be friends with her, it wasn't going to happen. Her and her friend that introduced us no longer spend time with my friends either now.

It's seriously getting depressing because in both of these situations I feel I did nothing wrong, but I'm losing friends because of dating these girls. I at least am avoiding dating coworkers, but even that's been difficult since I've been single. One coworker and I get along extremely well, she's tried to hook up with me a couple times in the last year, but I just feel that would be a terrible decision as well.

Thing is I'm terrible at meeting girls. I can't just go up to random girls and strike up a conversation and I feel that meeting girls this way should be a legitimate thing to do. Am I just doing it wrong?
Best to stay away from dating people you see regularly?
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