What’s the Worst that Could Happen? He Says No?

Some days, I’m comfortable with this half –in, half –out relationship with Stubborn. Other days, I’m at my wits end with it and want to give up now and cut my losses. So why am I not willing to rock the boat? Right now the most I’m even willing to ask him is to run errands, grab coffee, or just hang out around the house. And all I end up doing is think about asking these things and never following through. Why am I too scared to ask him on a real date if all I’m risking is this half relationship I’ve been trying to get out of for over a year?

“What’s the worst that could happen, He says No?” I don’t know why people say that. Rejection sucks. I’m scared of rejection. I’m scared the demons of my past will tell me I’m not good enough and confirm that I’m just a little too hard to love right now. I’ll blame myself for Stubborn’s lack of interest in me. It’s silly to blame myself since you can’t force anyone to like you and his feelings are actually out of my control. But still I might ask “Why am I too often only the friend or only the girl to date short term?”

And then he could say No to dating me but that doesn’t make me leave. Then I’m frustrated at myself, him, and the situation. I create a certain kind of hell for myself by staying with the guy who doesn’t want me. Or I mean, he does want me but only as a friend. Then it’s back to the ‘not good enough’ self –doubt. This type of frustration is like sandpaper on my self –esteem.

So say I do leave:

Maybe I’m scared of losing Stubborn. He’s been around for nearly two years now, he’s very much a part of my daily life. He’s loyal, non judgmental when I fear judgment the most, and smart. Of course, there have been days and weeks when we don’t talk but it’s not easy to forget someone you care for. Maybe, I like having a partner to keep me occupied with purpose and company.

Of course, there are other fears that come with the possibility of losing Stubborn. A constant companion suddenly gone would leave me lonely and bored. I like to think I’ve come along way with my mental health leading me to be self -efficient and self –satisfying. AKA I don’t need anyone to make me happy. But I wasn’t always this strong and I fear the possibility of regressing.

Or say he says Yes?

You mean he actually likes me? He really, really likes me?! I’m being a bit dramatic but it’s just because I’m proud he can finally show that he does want things to progress between us. He’s willing to risk the rejection, the heartache, and the failure if this doesn’t work out. But then what if it doesn’t work out? What if after this entire struggle to get him to date me, we find out that we don’t actually work well together and we should have just left it as friends. But now it’s too late for that and it’s too difficult to be friends as exes and I lose him just as I always feared.

The more likely scenario of him saying yes would be a repeat of history. We hang out once or twice and then don’t see each other for a couple months. And that leads me around the frustrating circle of Hell I mentioned earlier.

So No, the worst isn’t that he’ll say No. The worst is what he means when he responds. The worst is me having to decide what to do with that response. The worst is me realizing I still don’t love myself enough yet.

The worst is me saying No to myself.

*^ I wrote this a few weeks ago and therefore will have an update post tomorrow of what happened when I asked him out. Make sure to check it out!


  1. I tend to like resolution – like I need the answer to any unanswered question in order to make decisions about myself.
    Sometimes it’s not easy because the answer we don’t want is always a possibility, but at least it would be answered.

    Personally, I say ask him. ☺


  2. I say it doesn’t hurt to ask, but another part of me wants to say “don’t waste your time”. In my opinion, I find it interesting that if he says no, you’re scared of losing him when it seems you two can go weeks without even speaking to each other. So you have to ask yourself if you ever really had him to lose. Of course, I don’t know the whole situation but I feel like if you’re capable of going days/weeks/months without talking to him, I have no doubt that you’d be perfectly fine without him.


    1. Yeah, I’ve tried to leave him before which was when we would stop talking, and it was very difficult and emotionally taxing. One time I gave in and went back, another time he gave in and I took him back. There was always the safety net that we could reconnect and I wouldn’t lose him for too long. Check back tomorrow for the answer tho!


  3. I’m glad that you’re being so open and truthful about what you’re feeling. That’s the best way to get over inner turmoil. My only suggestion is to try and be at peace with your relationship status. I’ve been single for 18 straight years and do not legitimately see that changing but that’s OK! I’ll play the game if, and when, I’m ready.


    1. Thanks! Yeah I like honesty, I think it’s important. That is exactly what I’ve suggested in some of my past articles actually! Haha I totally agree with you, it’s just sometimes hard to follow your own advice. That’s great, I love your attitude!


      1. You’re welcome! It’s tough to listen to your own ideas sometimes. But that’s what motivates me to follow them. How can I possibly preach something I don’t do myself? I despise hypocrisy.


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