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The Hook Up: How to overcome fear of rejection

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.

Hi. This is kind of strange for me, but I am in desperate need of advice from someone who isn’t a teenager. I’m 14-I know, I’m just a baby, but I fear I may be in love with my best friend. We’re both openly gay to the majority of our friends and families, and have been best friends for about 10 years. She was the first girl I ever had feelings for, when we were about 10 years old. I’ve had little crushes and such and one long-distance relationship that was kind of bullshit to start with, but I haven’t stopped thinking of her in that way for four years. Every time I’ve seen her since, my heart has skipped a beat. She’s the only person that makes me feel valuable and lovable.

We act in a way together that makes it confusing for me to make a guess at how she feels about me. We don’t go to the same school, but we spend almost every weekend together. We talk every day, we cuddle, we hug for minutes at a time, we stroke each other’s hair, we kiss each other pretty much anywhere that isn’t considered sexual, we go to Tegan and Sara shows together, we joke and laugh and check out other girls together, and she’s dressed up as my boyfriend for various costumes. Our parents have thought-and suggested-that we’re together for years, along with everyone who sees us on the street. We’ve talked about living together in the future, fucking each other in bathrooms as college students, and are “practically girlfriends, minus the sex” (her quote). Despite all of this, I’m terrified of making a move with her because we used to call each other sisters and I’m afraid she still thinks of me that way. If I were to screw up our friendship, I’d never forgive myself; she is way too important to risk and I’d rather have her in my life as she is than not at all if I were to make our friendship awkward for her.

The one time I asked her if she had any other feelings for me, she giggled shyly and said I was reflecting my feelings onto her because she’s “such a stud.” So, all in all, I’m confused. She looks at me and talks to me and acts with me as if the feelings I have are mutual, but claims differently.

Should I listen to her very few, unconvincing words about this that she’s told me, or believe what her body language and actions tell me? Should I confront her about it, or wait a few years? Should I try to move on? Overall, what should I do?-R

Anna says: May I first say that I wish I had your eloquence and self-awareness as a 14 year old? Because, wow.

But also, yes, this situation does seem confusing. You talk about fucking each other in bathrooms five years from now, but otherwise have an affectionate friendship. You asked her how she felt and she dodged the answer. During that conversation did you tell her how you felt or was it strictly inquiring about any ulterior feelings she might be harboring? If you didn’t fess up, her dodge might have been a form of self-protection. Or perhaps her feelings are platonic and she doesn’t know how to tell you. You won’t know until take out the subtlety and ask her outright.

I think you’ll find some of the information from the first letter writer useful in your situation too, R. You have more at stake, but if you tell her what you told me–that her friendship is valuable and important and you don’t want to jeopardize that–I bet she will understand. I bet, too, that you are equally important to each other, and she wouldn’t throw you under the bus because you told her want to kiss her in places that are “considered sexual.”

It sounds like you’ve already blurred the platonic friendship lines anyway, you know? You’re in an ambiguous, semi-girlfriend stage, and this ambiguousness is affecting your life and other potential relationships and is keeping you in a kind of perma-crush state. Coming clean will help unconfuse things. Either she’ll accept and you can be hella gay together for realsies or she’ll say no and you’ll need to renegotiate some boundaries. Once you know, you can rejoice or move on, either of which is a better long-term state than the muddle you’re currently in.

One other thing that concerns me is this sentence: “She’s the only person that makes me feel valuable and lovable.” You are infinitely valuable and lovable. One person can’t change that, even though you may have Big Feelings for her, and vice versa. I just want you to know that.

To put it another way, as the amazing Cheryl Strayed wrote in Tiny Beautiful Things: “Whatever happens to you belongs to you. Make it yours. Feed it to yourself even if it feels impossible to swallow. Let it nurture you, because it will.”

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at annapulley.com and on Twitter @annapulley. Send her your The Hook Up questions at [email protected].

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