Is this crush worth pursuing?

What's the differences between one-sided love and a natural admiration? When is it worth it to pursue romantic feelings? He is my sister-in-law's younger brother. I have had a crush on him ever since I met him. I used to go out with my brother, my sister-in-law, and him a lot, and that's when I fell for him.

At first glance he was really good-looking but reserved. But the more I got to know him, the more I liked him. One time we wound up going out alone. He was outgoing and funny, and I was even more attracted to him. I thought that maybe he felt the same way, but when I talked to a friend of mine about him, she guessed that he was just being kind. She said, "He's just nice to you because he wants your brother to treat your sister well."

I've never stopped thinking about the possibility of being with him, but I wonder if I should give up. What should I do? Is this something I should pursue?

– Risky

It sounds like you need to spend more time with this man before you can decide whether he's worth the risk. You've hung out with him and the family, but you've only gone out alone with him once. It's possible that if you have more evenings with him one-on-one, everyone's feelings would be clarified. You might be more confident about what to pursue, if anything.

Is there a way for you see him, even if it's with your brother and sister-in-law? Perhaps it's time for dinner out. Or a movie night. Find out whether anyone is interested. It'll help you get out of your head and into reality.

If you see him more and suspect your feelings are real – and reciprocated – you can think about having a conversation with him about what's happening. You'll have to make it clear that even if there's rejection, you'll want to maintain respect so that you're both comfortable around the family.

But ... that's something to think about later. Much later. First you need to see how it feels to have him around – and whether he even shows up. If he's unavailable for simple plans, you should start letting go.

– Meredith

Readers? Is this too risky to pursue?