Why would a woman be upset if she thought she was "second choice"?

A little scenario: Jack meets Jane and Jill at a singles mixer. Jane and Jill are friends and Jack is interested in both of them. He would like to date both of them to see which one he is more attracted to. If Jack pursues Jane initially, then Jill, will Jill feel like second choice? I ran this by a male... show more A little scenario:

Jack meets Jane and Jill at a singles mixer. Jane and Jill are friends and Jack is interested in both of them. He would like to date both of them to see which one he is more attracted to. If Jack pursues Jane initially, then Jill, will Jill feel like second choice?

I ran this by a male and female friend. The lady said "Oh no, you can't go after both as they'll talk to each other and Jill will feel like second choice." My guy friend said "How the h*ll should I know?"

I also threw in this...Jill isn't second choice...she is more like 99th. Jack's first choice was the little red haired girl in 4th grade. Everyone is someone else's "second" choice, unless they both meet as virgins who've never dated anyone else, date, and marry each other.
Update: @Peyton and Ella: This is only a first date scenario. How would Jack really be "into" one or the other without spending some one-on-one time?
Update 2: I swore I saw the name "ella" instead of Alice.
Update 3: @Dark Eyes: I would actually welcome the competition. And it has already happened to me. I was interested in the same woman a friend of mine was. I asked if he wanted me to give him the first chance. He said "No. It is fine that we both try. In the end, she will be the one doing the choosing."
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