So I signed up for a free account last month on HowAboutWe.com as per your recommendation. I’ve been on a few decent dates through the site, but nothing to write home about. Until last week when I got a date proposal from this guy who’s profile pic looked oddly familiar Turns out it’s this kid I went to middle school with who I had the biggest crush on. I’m 90% sure this is a total coincidence and that he has no clue that we know each other. I haven’t seen him in over 10 years. Also, I was like super fat in middle school. Like… McDonalds fat. We have been flirting over email and I haven’t told him who I am, because I’m afraid he’ll want to cancel our date for this weekend. What do I do? He’s super hot and smart and I think he’s rich now.
PS- I’m really thin now so don’t worry about me.
Dear Carrie Mathison,
You’re sneaky. I like.
Here’s the deal: Your instincts are right. You definitely don’t want to tell him upfront. He could get scared away and then you will have wasted this opportunity. This guy could be your soul mate and by that I mean he might have a really huge dick.
You need to go on the date this weekend, look fucking amazing but not too amazing, be charming, and then tell him that he reminds you of a young Robert Redford. Guys love that even if they don’t know what it means. Let him really see you for who you are today: A young, hot, confident, honest-ish, catch, that any guy would be thrilled to take home for Hanukah. Then, and only then can you casually bring up the “where are you from” conversation.
Never let him know that you know. Just pretend it’s a total coincidence. Tell him that you don’t really remember him, but that you’re surprised that you don’t because he seems he has such an unforgettable face/jaw/eyes/smile. (just pick whichever of these makes the most sense for him).
Obviously give me the rundown once you sleep with him or not. Also, as I said before, I love that all you psychos are HowAboutWeing.