Ask Tinderella: Should It Be This Hard?



Love LOVE your blog – definitely the voice of reason to my many many Tinder dilemmas!

So I think I already know your answer to the advice I am about to seek from you, but I am just going to ask anyway because it would help to hear it from the horse’s mouth.

I met this guy on Tinder a month ago, and we have pretty much texted ever since. In the beginning it was more sexting, but as time went on we just banter, talk about our day, send silly pics to each other with a bit of flirting. He asked me out a couple of times but I couldn’t go because I already had plans, and in all fairness, I never suggested an alternate date. 

Last weekend, after too many wines with a girlfriend, I decided to text him and see if he wanted to have a drink with me.  As soon as he said he would like to, I freaked out and made an excuse to leave… I suck at this whole meeting up thing I know!

Anyhow, we continued to text but I can tell he’s over it. We actually had a couple of silly arguments since and I haven’t replied to his last message… he obviously knows I am still interested because I did ask him for a drink last weekend. The question is what do I do now? Should I casually suggest another drink or should I just leave the ball in his court? I know you are all about the guy doing the chasing, and I agree. But at the same time I feel I have also made it hard for him because I am guarded (ridiculous fear of being played by a guy and even a bigger fear of rejection) and not an easy nut to crack. Should it be this hard before we even meet?

Thank you so much for reading and would love to hear your advice!

Anonymous xx

Unfortunately, I think that the likelihood of this ending well is pretty slim – that is, assuming that you want to date this guy. If you’re just interested in a hook-up then I’d say go for it, I’m sure he’ll oblige.

So here’s the deal – forgetting everything else, I think this has been doomed from the beginning anyway, because of the sexting. Now don’t get me wrong, sexting is the best, but if you sext with someone before you’ve actually had sex, you are putting it in their mind that sex with you is on the table. If a guy feels that you are a ‘sure thing’ he might put in the effort to meet you once or twice, but he’ll become disinterested pretty quickly because it all came too easily. I speak from experience.

You asked if it should be this hard before you even meet? Honestly, no it shouldn’t! My instinct is to tell you to Tinder on, Annonymous Tinderella but if you really have to meet this guy then yes, let him chase you. And if he doesn’t ask you out after a week then you don’t have much to lose by asking him for a drink. Just be warned, he’s probably going to expect sex – so if that’s not what you want, make sure you have an escape plan handy.

With the next guy, try to be a little more open about meeting up if you really like him – it might help to remember that he probably is also feeling scared of being played and/or being rejected. It comes with the dating territory. Ultimately, the more that you put yourself out there, the less likely you are to be ruled by those fears.

Good luck and keep us posted!

Tinderella xx

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

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