I have had quite a few night stands (ONS) over the past year (about 25).

I usually have one of the following feelings afterwards:

1.) I do not really want to see the girl again
2.) I do not mind hanging out with the girl again, whether that be FWB type of deal, or just a cool chick to do something with
3.) I develop feelings of infatuation for the girl.

Number 1, is not too hard to deal with. Sometimes I have to be direct, or sometimes I gradually distance myself if the girls gets clingy.

I have problems with 2 and 3.

Number 2: Whether or not I decided to hook up with the girl again, I do not hint at a relationship, and I keep things casual and emotionally light. If I do not want a relationship, should I be keeping these girls around? I think some may stick around because they want a relationship but I am not sure. Should I ask if they want a relationship? Should I be really direct and just explain that I want to be just friends or FWB? Since I am a free-spirit type guy, I have just been going with the flow without much emotional confrontation or exchange.

Number 3: This one has happened a few times to me, and is really problematic. One developed into a short lived relationship of 4 months, the girl and I are still on good terms and talk. Another one got ugly, I believe the girl was testing for a relationship, and I got confused. Anyways we never had sex again, though we saw each other a few times. The exchanges we had were just emotionally frustrating. I am not sure, what she was feeling, and she probably felt the same way about me. Should I just force myself to forget about these girls? Stay aloof, and let them do the work if they feel the same way? If we both want to keep hanging out, should I just stay FWB or consider the possibility of a relationship?

I am number 3 right now, and I do not encounter the situation much so I do not know how to deal with it. When it comes to women, specially ONS material, I am aggressive and dominant. I like to take the lead, go for the close, and overcome obstacles. All that being said, after a ONS, it feels like I reached the finish line already. Sometimes I feel odd aggressively pursuing the girl after a night of casual sex. I am not sure pursuing the girl for anything other than FWB is a good thing, but what the hell somethings you have to go with your gut and deal with the consequences.

Anyways thanks for the help guys.

Relationships are not the ultimate goal of dating. They are a goal, not the goal.
You don't have to ask them anything. Enjoy yourself and the time you spend with these girls and let things follow their natural course. If they want more, you can make a decision then and there.
Same as above. You seem to have some issues in the sense that you are unaware of what it is you actually want. Do what you wanna do. It's that simple.
ONS by their very nature are not congruent with relationships. Not saying it can't happen, but it's harder to enjoy the hunt when you get the kill before it even starts. For me it simply doesn't work.

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Honestly, it's hard for me to transition from one night stands to anything else. I got the kill...so I'm like eh. Not fun anymore. If you want to keep girls around I recommend not taking them home the first night and slaying next time. Now, this might seem counter productive if you have it in the bag, but I have been able to keep girls around more after I started implementing this. Rather than sleep with the once, I go on dates, they take care of me, pretty much just increased my social circle and I can bring her out with friends.

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