I’ve recently developed a crush on a pansexual, single friend of mine. I’m not usually emotionally attracted to people the way I am to her (and, you know, her being hot doesn’t hurt). We’re pretty touchy feely with each other and she usually seems so happy to see me that when she doesn’t pay special attention to me I fall into that 80-year, Pablo Neruda-quoting cycle of despair you once detailed. She’s really special and I want to go for it, put I am usually attracted to people who are assertive and act on their own feelings very clearly. I have no idea if we’re friendly or flirting and terrified of rejection. Is there a way to let her know I’m interested without wearing a sign that flashes “platonic” or “super gay” for every interaction I have?
Anna says: Well, definitely stop wearing your “platonic” sign around her! That will only confuse things.
Here’s my somewhat-condescending-but-I-don’t-mean-it-that-way advice. Become less afraid of rejection. Being “terrified” of asking someone out will not serve you in any lasting way. Indeed, that kind of fear may seep into other areas of your life, like when asking for a raise at work, confronting your roommates about leaving their dishes in the sink, or even when trying to tell a lover what floats your boat in bed (or in an actual boat, whatever).
Fear is an extremely useful emotion when one is being charged at by an angry moose, for instance, or when rescuing kittens from a burning house. But when it comes to telling a girl you want to see her naked? That is hardly the stuff of terror. I’m not saying it’s not hard, or that your palms won’t sweat, or you won’t feel a little bit crushed if things don’t go your way—it is and you might!—but those aren’t good excuses for living your life in a state of paralysis.
So, how do you overcome fear of rejection? This is going to sound contradictory, but you do it by cultivating an even bigger fear of regret. Meaning look at a potentially scary situation (in your case, asking out your hot, pansexual friend), and then imagine all the awesome things you would miss out on if you did nothing.
I had a friend years ago that I had a serious crush on. We would flirt and banter but it never went beyond that because I was too much of a chicken to do anything more and risk my precious ego. Years later, she found me on Facebook and admitted she’d had a crush on me too. By then, we didn’t live in the same city and I had a girlfriend, so it was too late, but I was pretty disappointed that I didn’t go for it back when I had a chance. Taking a risk on someone who makes you feel awesome is almost always worth it, even if she might not feel the same way.
I know that one of the biggest concerns of asking out a friend is that you’ll jeopardize or ruin the friendship. And this is valid. Friendships last longer than relationships, by and large, but it’s pretty rare for an admission of feelings to destroy a solid friendship in any kind of lasting or meaningful way. Here’s another story, one example of the many rejections I’ve faced from women, and have survived relatively unscathed! When I was getting over a breakup, I was set up with a smart, cute girl who I will call Wendy. Wendy and I ended up sleeping together on our first date, and then not we didn’t talk for a while, and then we became friends. Then we slept together again, sort of randomly, and I started to wonder if maybe there were feelings there, after all. So I texted her (as an aside, don’t text your feelings! Because then you have to agonizingly wait for them to respond, if they decide to respond at all!) and she told me she’d rather be friends, and we had one awkward, process-y coffee date to settle the dust, and that was it. It wasn’t a big deal, and in the end, I was glad I told her, even though it made my stomach do a queasy-flippy thing for about half a day.
Another way to take some of the sting out of rejection is to detach it from its weight. Rejection doesn’t mean you aren’t desirable to women. It only means you weren’t desirable to this one particular woman, during this one particular time. It doesn’t mean you’re ugly or dumb or terrible at putting IKEA furniture together. So don’t treat it that way.
Now please go tell your hot friend that you’re interested in her. Be direct, confident, and unapologetic. Give fear the finger it deserves. You got this.