Dr. Date

Dear Dr. Date,
I’m twitterpated over the nicest guy I’ve ever met. The thing is, he’s such a great person, I can’t tell if he’s flirting with me or just being awesome. I suspect the latter, but how can I know for sure? And let’s be honest, I’d probably be happier just pretending he’s flirting than admitting it’s hopeless.
—Decidedly Delusional

Dear Delusional,
Ask him out.
— Dr. Date

P.S. I think the next letter may interest you.

Dear Doctor,
There is a girl I am sure likes me, and I share the same feelings. I am not the kind of guy who can ask a girl out just on a limb, so I’ve just decided to wait for her to make the move. Is it unreasonable to wait for the girl to make the move? Or am I going to find myself demoted to the friend zone if I don’t act?
—Waiting

Dear Pussy Willow,
First, read the letter at top.
Second, so you’ve put your foot down and “decided” to wait for her to make the move? Sounds a lot more like you “wimped out.”
Third, you are “sure” she likes you and yet you still consider asking her for a date going out “on a limb”?
Fourth, if you don’t make a play for her, you deserve to be in the friend zone. Go lace up your Air Jordans and slam dunk this gina.
We’re rootin’ for ya, pal. Even if you don’t deserve it.
—Dr. Date

Dear Dr. Date,
I recently celebrated my six month anniversary with my “girl”friend. She had a doctor’s appointment a few weeks ago but was very discrete about what details she passed on to me. I thought, perhaps, that she had an STI that she didn’t want to tell me about because she thought it would hinder our relationship. But I loved her, and I knew that something like that wouldn’t matter, so I kept bugging her about it. Finally, she gave in and told me that three years ago, she was a dude. I don’t know what to think about this. Half of me is grossed out because I don’t want to be dating a dude, but the other half of me thinks that’s shallow, and I should just love a person for who they are. What should I do?
— One Of These Things Is Not Like The Other

Dear Half ‘N’ Half,
First off, if you weren’t able to notice for six months, how is it an issue now?
Just because your significant other was born with an inconsistency between what gender she identifies as and which sex was chromosomally shackled to her mortal coil doesn’t mean there’s a reason to break up. Your girlfriend was always a girl, she just came wrapped in the wrong packaging. Sex is biological. Gender is a construct.
With most of what you need to know to major in gender and women studies out of the way, let’s have a little man-to-man-to-woman talk.
That slightly dogmatic preamble wasn’t to say that you’re not entitled to being turned off. Feeling so doesn’t make you a bad person, but breaking up with her in a disrespectful way might.
However, there are some subsidiary issues at play.
First, why did it take some “doctor’s” appointment for said girlfriend (I will not acknowledge your quotation mark douchebaggery) to disclose her transgender status? Aren’t you more concerned that she would hesitate to discuss an STI she has? (Which, last I checked, are a little more harmful than having sex with a surgically constructed vagina.) You say it’s only been a few weeks. Part of the reason you may have had an adverse reaction is because it sounds like you were informed in a rushed, high-tension context. Really though, does this fact compromise your sexual attraction to your girlfriend? You wouldn’t be a jerk to admit it if it does. We all have our own tastes. As a rule, I don’t date anyone who isn’t into leather (hello, Rob Halford).
I think a lot of people often ponder a situation like yours as one of those noodle-scratchin’ hypotheticals. Some people would be able to handle something like this or brush it off as irrelevant. Maybe you’re not the type.
But on to the meat ‘n’ taters of your letter. Here’s my take:
You say “half of me is grossed out because I don’t want to be dating a dude.” You’re not. You’re dating your girlfriend, who is, as far as I know, currently a woman. “Half of me thinks … I should just love a person for who they are.” Yeah that’s cute and all, loving her for who she is. But this is part of who she is. If you can’t jive with that, then that’s fine. Maybe she doesn’t like things about you either. But really, quit muddling your situation with vague generalizations that you would apply liberally to the rest of your life, and look at whether you truly are mentally and physically attracted to this girl. If not, you owe it to her to be honest about it while also not being total knobjob.
—Dr. Date