Well, Ted could have asked Maggie right away since she has tendency to get into the relationship right after break up. Instead of asking her right away Ted tried to keep her away from other guys, i mean she would have said yes to Ted given her past relationships how she got into all the relationships right after a break up. Ted could have asked her out, gave her some time to think, go to the college. Ted should have let Maggie know his feelings for her. Ted's a man with a plan but with poor execution.