Let me give you two, nay three, examples of bad timing that have caused me grief since I started college almost 4 years ago...
The summer after my freshman year I started dating a girl. At the very beginning of our casual relationship she says "I need to be single when I go off to college, so we have to stop dating at the end of the summer". I spent all summer with that in mind so that when the day came I was prepared, but just as sad as I would have been otherwise. Well, this girl didn't get over it quite the same, and at various times my feelings for her have returned. But we both know that because of the fact that we go to school 2,000 miles away, and she has one more year to go than I do, so we know it's not realistic right now.
Last year, I started dating a senior in January. This was the girl that I had been crushing on since day 1 of college. I knew she was staying in the area after graduation so I figured maybe we could make it work after her school year ended. Lo and behold, when I asked her what she wanted from the relationship she promptly ended it saying "When I graduate I need to be completely done with college. I need a clean break". I understood, but was definitely upset.
And that brings us to now...I'm graduating in May, and I have recently started causally dating a younger girl. She's amazing, and not someone that I had any intention of being with before it just kind of fell into place. I tried to keep it as low key as possible, but the more I spend time with her the more I fall for her. I've still gotta tell her that, but the only reason I didn't pursue it more seriously from the start is because a few months after graduation I'm leaving the country for at least 8 months...and I don't know how she feels about long distance. Hell, I don't even know if I'd give it a shot. It's hard.
TL;DR-yeah, bad timing is very real and it is sort of the story of my dating life.