Finally ready to ask out a crush but I’m scared. Any advice?

 ThatDidIt1990 says:

Sorry if this is kind of long but I at least need to get it out of my system. Basically, I’m a overthinking bastard but here it goes. I (M24) am really into my coworker (F23) and it’s to the point where I finally want to ask them on a date (which rarely happens to me). I think that we both share mutual feelings for each other but there are some mixed signals. 

  • She always smiles and laughs around me, blushes occasionally and focuses on me in group settings. We share all the same interests. She likes to show me things/photos that we’d find interesting. The other day, she suggested we see a concert together so I know she has to at least like being around me a little bit.
  • However, both of us seem to be really reserved/shy so there isn’t much physical contact (plus it’s in a workplace. plus I’m a wimp). There was a movie she owned that I wanted to see and she’d let me borrow it but she kept forgetting to bring it over. Wouldn’t she remember it if she wanted me to check it out? She is one of the priorities in my life right now but I don’t feel that I’m one of hers. Maybe it’s true or maybe it’s just me.

Like I said, I’m a overthinking idiot with bad direction. So please, any advice is appreciated! Whether good or bad news, I need to calm my mind.

Demetrius says:

As is often the case with coworkers, my first piece of advice to you is to make sure it’s okay to date your coworker based on your company’s policies. Assuming it’s okay, then ask yourself: if the worst case scenario happens, whether it’s an initial rejection, rejection after a couple dates, or you end up in a LTR then breakup, will you be able to still work with them? If you think that you can, even after all of this, then we at least have that covered. Once we take the coworker factor out, the real issue is that you either don’t know how to ask your crush out because you’re not naturally aggressive, or you’re afraid of doing it. Let’s tackle the fear first, then the how-to later.

Let’s talk about your fear. You may never be able to conquer your fear of rejection or your shyness, but the best you can do is accept it, acknowledge it, and just do the things you’re afraid to do. Here’s a simple truth that you have to acknowledge whenever you’re afraid of saying or doing something that will hurt you emotionally: It changes nothing. Yes, it can change how you feel by making you sad or angry, but that’s only if you allow yourself to feel that way. You can’t control your instincts, to move away from the things that make you afraid, but you can make the conscious choice to move through your fear. You’ve been doing this since you were a child, whether you realize it or not. You were probably afraid the first time you swam, or started a new job, or a new school year, or drove, or flew, but you did it anyway right? Well good! If you, as a child, could survive the first time you hopped in a car or on a plane, you will definitely survive asking someone out. Driving and flying can kill you, rejection can’t. The worst thing about a rejection is the mental pain it can cause, but that’s only if you let it hurt you. I’m not saying that you should suppress your feelings, I’m just saying that you should put them in perspective. At 24, getting rejected sucks because your dating life is brand new. What about at 40? Do you think the rejection you receive today is going to matter then? No? Well good, that means it doesn’t matter today. It sucks, but you’ll get over it. If you choose to get over it sooner rather than later, you’ve got nothing to worry about. Remember, your fear might be driven by instinct, but your reaction to it is a choice.

As for tips on how to ask someone out, you know, sometimes it feels like I’m belaboring the obvious, but here it is again: Communicate. Specifically, use your words and make sure they have clear intent. If you like someone and want to go on a date with them, that’s what you tell them. Not “I think we should hang out“. I think we should hang out, or in your case “You should bring over this movie that you own because I want to see it” is open to way too much interpretation. “I’d like to take you on a date” or “Come over, bring this movie, I’ll cook (or order in) and it will be a fun date” is way more in line with what you want to do. As children, most people are taught to speak with manners and not to say exactly what’s on their mind, but I think you need to go back to your inner child a bit. As kids, we told the people we liked if we liked them because we didn’t have the vocabulary for double-speak. “I like you, let’s be friends” is something I remember saying as a kid, I’m guessing that most people can remember saying that or hearing that. What’s wrong with saying “I like you, let’s go on a date“? Nothing. So do that, take a risk, and hopefully you’ll be rewarded.

As for the last part, where you’re concerned that maybe she’s not making you a priority, well it seems to me that because you haven’t made it clear that she’s a priority for you, she isn’t going to make you a priority. You asked her for a favor and she didn’t follow through on it, no big deal. You’re the one who has to take action if you want to pursue something serious so go do it!

Remember, don’t over think it, don’t let your fear rule you, and be direct when you ask her out (if you can and think it’s a good idea).

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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