I’ve asked her out a dozen times and I always get a NO. Will she ever say YES?

datinganonymously asks:

I’ve asked her out at least a dozen times, and she’s never said yes. She heavily blames social anxiety, but we work in customer service and I know she has other friends.. Am I just barking up the wrong tree? Yes, you read that right. She is a co-worker. I don’t care about that part, but she might. So its poignant.

Then long and short of it is that we met almost a year ago (july) but I didn’t really get to work with her until about Halloween when I transferred departments. Since then we’ve developed a great rapport and working relationship. I asked her out to lunch the first time for Valentines day because I knew we were both single and didn’t really believe in the mularkey of the holiday (we spent a portion of that day bashing on people who do). She turned me down and I figured at the time it was for the symbolism of the event and she didn’t want to give me any ideas. About 2 weeks later I asked her out again and she used the reason of homework to turn me down.

Over the course of the next month or so I asked her out a few more times and she used a social anxiety complex to say no. I think she is a cool person so I decided to get to know her without going out with her, and started conversing over facebook. Within these conversations which take place over many hours, I’ve come to find out that we would be quite compatible with our hobbies and interests, but we’re different enough to keep it exciting. Even when she says “i’m a homebody and a loner” it’s endearing to me because I feel I’m the same. So. We’ve been talking almost daily over fb for well over a month now and I feel like we have a serious click, but she still won’t say yes when I ask her out (she compared it to a Tootsie pop yesterday “how many licks does it take to get to the center?”).

That’s the dilemma there. We chat, she smiles radiantly when she sees me, and we really do have some deep connections, but she doesn’t want to leave her house to [insert activity here] with me. So, what’s the deal, yo? Should I quit asking and let her figure it out? Am I just spending unnecessary energy on a woman that’s not attracted to me?

Demetrius says:

Oh boy. Sometimes I choose questions that have some real substance and require some real thought and consideration but today, luckily, I’ve given myself a really easy out today.

Let’s get your questions out of the way before I go on my rant. It’ll be short, and it’s less about you, and more about your mindset.


  1. What’s the deal, yo?
  2. Should I quit asking and let her figure it out?
  3. Am I just spending unnecessary energy on a woman that’s not attracted to me?


  1. She’s not into you and she’s trying to reject you in the nicest, most indirect way possible
  2. Yes AND just assume that she’s already figured it out. She’s not into you.
  3. Yes. She’s not into you

Now that we’ve gotten that out-of-the-way, let’s talk about your mentality. You seem like the type of guy who wont take no for an answer unless that no is so blatant that it’s insulting. It’s the same sort of mentality that self-professed “Nice Guys” have. The idea that you can get of rejection, or the Friendzone, by using logic. We’re a great match so naturally we should be together. I’ll just show her how great I am and she’ll change her mind” The fact of the matter is this: A rejection is a rejection. Your persistence after receiving numerous rejections tells me that you consider yourself to be owed her attraction because REASONS. This isn’t a dilemma, it’s all pretty straight forward. Despite the fact that you try to make it into an issue of her having social anxiety and maybe that’s why she’s rejecting you, it’s pretty clear that she is not into you, nor will she ever be into you.

Here’s your situation without all the fluff:

  • You asked her out, she refused
  • After a year of knowing her, you keep asking her out. She continues to refuse you
  • She is friendly and nice to you but has given you no sign whatsoever that she might be attracted to you
  • You’re confusing conversations and common interests as attraction and compatibility

Why are you even still asking her out? More importantly, why do you think her answer will change? Setting aside the fact that your entire line of reasoning for why she should go on a date with you amounts to “She’s basically bullshitting about her anxiety issues” and “We’re totally compatible because we speak daily and we have things in common”, you also keep coming up with reasons why she might say No to a date with you besides the most obvious answer. It’s not the significance of certain dates, or the fact that you work together, or any other fantasy you might have that romanticizes your unrequited love. To paraphrase…

She’s just not that into you. 

Stop wasting your time, stop pursuing her, stop making excuses for why she might reject you (because quite frankly, it’s insulting) and just move on.


Take her at her word when you ask if she wants to go on a date and she says No. If someone is really interested in you, they’ll find a way to make a date work. A year into knowing her and she hasn’t said yes to any of your dates…you have to know that means something.

Good Luck Out There.

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