L.C.
Confused is good. In fact, confusion is exactly where you need to be right now. Adding another person and their demands and whims to that will not make you a happier person, no matter how lonely you are.
Clearly, you have struggled to find partners who are actively good for you, who bring something positive and loving and supportive to your life, and going right back at it (5 months IS 'right back at it) would be the best way of finding exactly what you left the last time.
I think it would be appropriate for you to stop asking your son what he thinks you should do. You are the adult, he is not, and his opinion of sexual/mating relationships is going to be entirely based on what he thinks you expect or want him to say.
You need to learn how to make friends. Join the PAC, or find a service club so you can work alongside people who are doing something for other people. You need to find a way to give to others, so you can find other people who do that. Invite potential girlfriends in for tea or to go through your closet with you, help you sort out your son's hand-me-downs, or to swap clothes you no longer love or fit.
When you have at least two friends who are supportive, positive and who give you as much as they demand from you (or more, which is a good position to be in), you will be stable enough to find a man who will be supportive, positive and give you more than he demands from you. Until you have at least 2 live friends who are in that category, you will be willing to accept anything to feel loved, even if it is pain, shame and fear.
Oh, and stop chatting with guys online. Chat with moms online, chat with volunteer counselors online, chat with women seeking friends online, chat with grandmothers or aunts or expectant mothers. But stop talking to men online until you have your 'real life' sorted out enough to be able to spot the losers.