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How Late is Too Late?

After flirting off and on via text and email, I finally went out on a date with a guy that I thought was pretty cool. After the date, we still stayed in communication for awhile. One day, he'd apologized for not being as chatty, he said that he was having custody issues with his ex-wife. I told him I understood and take all the time he needs, his kids come first.

A few weeks later, I checked in on him, he thanked me and told me what had been going on. It's been almost two months now since we last spoke and I've been wanting to initiate communication with him again. But, I'm afraid of getting rejected. Should I just say screw it and get it out of my system? Or should I just try to block out thinking about him? I have been on dates with other guys, but I just haven't clicked with them as much as I did with him.
How Late is Too Late?
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