March 7, 2012
How to be upfront in a non-awkward way…
I was emailing back and forth tonight with the guy who I sort of maybe know from school- the one who contacted me on my favorite internet dating site. Let’s call him D.
D seems like a really nice guy (But don’t they all?) One of the taglines on his dating profile is that he is not looking for casual dating. (But don’t they all say that?) He asked me out for drinks or coffee at a time TBD. Hopefully this will occur after my appointment with my therapist, because I need some professional advice on how I screwed things up last time.
I know she will give me more of the same advice that she did with R (that I did not follow). At our (mine and potential date’s) age we are looking for something more serious than when we were teenagers. This justifies asking real questions about what really matters. Instead of asking “What toppings do you like on your pizza?” I need to ask “What are some of your life goals?” Instead of asking “What’s your favorite color?” I should be asking “How do you feel about raising someone else’s child?” Instead of being scared of scaring a guy off, I need to ask “Are you dating anybody else right now?”
This will be difficult for me. I have said it before and I will say it again, I am seriously awkward on dates- first dates especially. If I don’t have a list to go over and rehearse beforehand, I will only ask him if he has any pets, not what he’s looking for in a relationship. So here goes the list making again. I will compile a list of questions before our date and then commit it to memory. This should allow me to be upfront without being entirely awkward, and also get some answers to questions that really matter to me.
misadventures of my awkward dating life 