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I'm sure its just a phase and if anything you are kind of encouraging it by continuously asking if he likes/loves members of your family. He also may be noticing on some level that its getting a reaction out of you when he says no, so, he keeps doing it.

Its never occurred to me to ask if LO likes/loves our family members - because of course she does!

I would probably just stop asking if I were you! My eldest (2.5) used to really dote on his baby brother, but once baby brother got mobile and started getting all in his stuff, he was NOT a fan. They don't seem to get along (baby is constantly destroying/taking whatever toddler is doing, and toddler's constantly yelling at him, pushing him away, etc). But I think that's normal. And sometimes older brother will state that his brother is "my best friend!" so I know they love each other, even though they get on each other's nerves!

@Raindrop: I get that, I'm just not sure taking temperature checks on feelings keeps rivalry away. For peace of mind though, as one big sis that stopped liking her baby bro as soon as he became mobile and a general nuisance no matter what I always had his back. Looks like @Adira: has noticed the same with her boys.

I would just stop asking. Does it really matter at this point? The baby is just a baby! Eventually, they will develop a relationship and will like each other (or not) for real and then you will know. All that you can do is make sure they don't beat each other up or do evil things to each other

If he brings it up on his own, I would listen, and see what he says. Sometimes it's just about the attention the baby is getting. You can say something like "sometimes it's very hard to share toys" or "sometimes it is very hard to be a big brother" etc.

@hummusgirl: I love your advice! I hate, as an adult, when I share my true feelings and people tell me I shouldn't feel that way, or criticize/judge me for my feelings.
I try to keep that in mind with me LO, it's easy to laugh when he gets mad/hurt over something that an adult wouldn't, but I check myself that his feelings are just as real and valid as mine, and I need to show him I respect him by acknowledging that.
I agree with the others about probably just stop asking. I definitely don't remember my mom ever asking me if I liked my siblings - and I had five of them! And there were definitely times I did not like them. and honestly until I was an adult, I didn't even like one of my siblings. I never thought about my mom's perspective on that though, so it makes me wonder if it upset her!