Asking the girl questions about her dating life gives him some perspective about how much dating experience she has.
He may even want to do a comparison between how much experience he has in dating and how much you have.
He wants to understand how he should go about interacting.
If he gets the impression that you haven’t had much of a dating life, he may have a better idea of how to go about talking to you.
He would know at this juncture that he can probably get away with messing up a few times with you.
If you have barely had a dating life, you may not yet know what constitutes a guy that would be your most compatible match and what doesn’t.
However, if he were to learn that you have a very experienced dating life, he may understand that he would have to use a more cautious approach with you.
He knows that he will have to be more level-headed in how he goes about talking to you.
He knows that you would most likely be privy to any tricks that he may pull in trying to seduce you during conversation. Hence, he may try to play it really straight with the experienced girl.
When this guy on a dating site asks a girl questions about who else she is meeting, he may be curious about the kind of competition that he is facing.
Being that you are on a dating site, he already knows that there are most likely other guys who are talking to you or trying to get your attention.
He may want to get some kind of gauge on how many of these guys there are.
Guys are often in the habit of wanting to know this kind of information.
Gaining this information often gives them the opportunity to either up their game or just quit entirely.
By getting an idea about how many other guys that the girl may be meeting, he will get an idea about how many other guys that he is competing with for the girl’s attention.
He would also hope to gauge just how well those conversations are going with those guys.
In other words, in asking the question about who else the girl is meeting, he may want to get some kind of read of how emotionally invested she is in those guys.
If he gets the sense that there is a guy who is really making you feel good emotionally, he may use that opportunity to downplay the effect that this guy is having on you.
He may start by innocently asking you for a little bit more information about the guy.
If you divulge that information, he may tell you something negative about the guy.
He may say that he has known guys like that in the past and you should be careful.
He may even say that something just doesn’t seem right about the guy.
In doing this, he is hoping to plant the seed of doubt in your mind about the guy.
If you start worrying about the guy that has been having such a good emotional effect on you, you may approach your future interactions with that guy with more caution.
The seed of doubt that has been planted in your mind may keep you from fully allowing herself to become emotionally attached to that guy.
This was the intent of planting the seed of doubt in the first place.
Now that you are no longer allowing yourself to become emotionally attached to the guy, you become unconsciously more trusting of him.
This is the trust that he hoped to gain in planting the seed of doubt in your mind.
With that threat out of the way, he can now take advantage and try to get you to start liking him even more.