And yes..people do question others to excess, which is obnoxious For example, think about the woman in the bar who asks you about your suit, watch, the car you drive, what you do for a living, etc.
Taken to extreme, this hides someone else's insecurity and low self-esteem by "judging" others. If the other person is at all interested, he or she will continue the conversation.
They are trying to "earn" the other individual's interest, attraction, or affection. Ask them if a piece of clothing on them is a designer label.
Essentially, they are opening themselves up to "being judged"...rather than evaluating, qualifying, or screening the other person. Suspend your attraction to them and make them jump through a hoop or two to prove themselves to you. Ask them how they take their coffee (and tease them if it is gross).
Rather than "putting yourself out there", get the other person to invest a little first. Or, "could you watch my stuff for a minute while I get a coffee"? I have discussed the reason for this "investment" effect elsewhere (see here and here).
Fortunately, there are a number of ways to approach and start a conversation, without opening yourself up to evaluation.
Furthermore, they are just as "confident" and "assertive" as putting yourself out there directly.
Known as the Ben Franklin Effect, it is the phenomenon where people like others more when they do a favor for them (Jecker & Landry, 1969).
That is, when the OTHER PERSON does a favor for you, THEY like you more.