Ask Tinderella: He Thinks I’m Crazy, But Can I Win Him Back?


Hi Tinderella!

Before I start I just want to say a big hearty congrats on finding your bro, maybe there is hope after all.

Okay now the juicy stuff.

I recently matched with a seemingly nice guy on Tinder. We texted (aka weird texting flirting) and all seemed well – he had initiated it and seemed into me. The only small hang up was that he was out of town on vacation but would be back in a week or so, which was fine. I had recently made myself a promise, however, stating that I wouldn’t put any more emotional effort into long talks/texts before meeting up. It’s happened too many times that we would talk and something would come up and the actual date part would never materialize.

Anywaysssssss, so I sorta broke my own rule with this guy by talking, but he was out of town so cut me some slack! Alright so a few days in he sent me a picture of himself and all I saw was a ring on his left finger (it was a mirror selfie eww I know, so I stared long and hard to make sure it was on his actual left hand)…… I stared at it, willing the ring  to get up and move itself to his other hand but alas it remained in place – Newton’s law or some shit like that. I kept my head and said point blank, ‘That’s an interesting ring on your left RING finger’, and do ya know what he did.. he laughed at me!

Ashamedly this is where things went south, girl rage texting ensued and to top it off he didn’t say anything back, all I wanted was him to deny it and he didn’t. Okay stay with me here. I didn’t think things could get worse but wait for it, he has different distinctive tattoos on each arm, left and right so, I turn to my sister to see which side she thought the ring was on. I screenshot some pics of him and sent them to……him…….not my sister, in my haste I accidentally sent them to him not her. 

Yes, I involuntarily threw my phone at the wall when I saw what I had done. He did not respond. Classic guy shutting down because this girl is crazy. The next day I attempted to make light of the situation, I got ignored. Later I tried once more and he finally said and I abbreviate,’You’re crazy it was on my right hand’ blah blah blah and to top it off he didn’t even know what I was talking about (girl speak sometimes doesn’t translate to guy speak I guess). Apparently he did not pick up what I was talking about when I asked what was on his finger!

So Tinderella what should I do? I made a mistake, attempted to fix it and made it worse I think. I really like him but I’ll be the first to admit I kinda messed this one up (come to find out he’s not married) I attempted to make light of it and move on but I’m pretty sure he thinks I’m super crazy. Is there any fixing this?

Yours Truly,


Oh oh, that was for sure juicy stuff. Before you start kicking yourself for showing the crazy too soon (a girl after my own heart), I’m curious as to why you are certain he isn’t married? It kind of sounds like he is… I just don’t understand why he would be wearing a ring on his ring finger if he wasn’t? Before you readily believe him, I’d try to do some digging on Facebook or LinkedIn to see if there’s anything incriminating on there. 

If we assume that he’s telling you the truth, then yes, your outburst likely confused him and/or freaked him out a little bit. You unleashed the cray before you’d even met… I’ve done this many times and it rarely ends well. Is it salvageable? Yes, potentially. 

Ok, so if you actually want to meet this guy (and I’m not his biggest cheerleader, honestly, but do your thing) your best bet is to pull away completely. Don’t text him or contact him in ANY WAY. If he gets in touch, send him short text messages – don’t be rude, just don’t overshare or ask a lot of questions.

You’ve already given him a way bigger dose of your personality than you had intended to this early on, so now is the time to pull back. The more breezy you are, the more he’ll chase you. It’s messed up, I know, but 9 times out of 10 this works.

If he doesn’t contact you, then leave it for a few weeks – maybe go on some dates with other people to distract yourself – and if you still want to meet him after the time has passed, then send him a text saying, ‘Hey what’s up?’ Hopefully this will prompt a conversation leading to him asking you out, but if it doesn’t then at this point you should just cut your losses and move on to the next.

Whatever happens, please know that you do not stand alone in the I Sent Regrettful Texts That In Hindsight Might Make Me Look Crazy Camp. I’m right there with you.

Tinderella xx

Do you have a dating question for Tinderella? Email your questions to with the subject ‘Dating Advice’.

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