I Cancelled a Date — Now I Regret It

Dear Dating Diva, 

This girl asked me out back in December for dinner, but I cancelled the day of our date. I apologized to her over text, and I saw her for the first time this semester at FS this past weekend and I apologized again. She said, ‘It’s okay, no worries’ and nothing else, no mention of rescheduling. She’s probably mad, and rightfully so. I think I’ve blown my shot with her. If I could go back in time, I’d do it all differently. Do you think I still have a chance? What should I do? 

Help a guy out, 

Messy Manny 

Dear Messy Manny, 

You’ve put yourself in a tight spot. It definitely sounds as though you’ve annoyed her with your flakiness. But before I discuss solutions, I need to ask one big question: did you ask to reschedule your date with her? Either at the end of last semester or the beginning of this one? If not, she probably thought one of the following: that you lack follow through/initiative, that you’re disrespectful, or that you agreed to the first date out of pity and cancelled when you couldn’t go through with it. None of these are good opinions of this girl to have regarding your character.  

Now before you come whining to me about how ‘you thought she was the one who was supposed to reschedule’ I’d like to point out that as the canceller it is your job to reschedule and to not do so is rude and a little disrespectful. This applies to any situation, whether that’s hanging out with friends, meeting with your boss, or most importantly, dating. Your ignorance towards this nicety will not fly as an excuse to this girl…she deserves better.  

Now let’s suppose you did the proper thing and asked to reschedule…did she leave you on read/delivered? In this case, cut your losses. She is the rude one in this scenario. Life happens and sometimes you have to make a last minute cancellation, but it is out of your hands if she chooses not to reschedule.  

Let’s say you were the rude one. Your next step is to explain yourself to her and hope for the best. Say something like ‘Hey, it was great to see you at FS! I’m really sorry about what happened in December, and I was wondering if you’d like to reschedule.’ It’s scary knowing that she’s probably and rightfully upset with you, but you need to put yourself out there if you want a second chance. I can promise you right now the only thing you’ll become if you don’t, is a funny story at brunch with the girls. She put herself out there asking you out, now it’s your turn to put yourself out there. 

Don’t mess up take two,