Hi Jen! I was just wondering is there a limit to how many times one can ask the same boy out and get rejected each time? I have asked the same boy for caffeine or alcohol based beverages three times and each time he has essentially declined. From a fellow height challenged beour. XXX
Hello Fellow Petite! This one hits fairly close to home, so this advice is as much for me as it is for you, so we’re in this together. I’m going to be brutally honest here – stop in the name of sanity. Once was enough. I speak as someone who has been there, done that, and ruined the friendship. You’re verging into self-harm territory if you go back there again.
If you think he’s giving you signals that he wants more, he’s more than likely just enjoying the flirty banter with someone safe; and who is safer to flirt with than somebody who has asked you out? Doesn’t mean it’s right though, but it does happen. Ego is a bit of a bastard really.
On the plus side, after three times getting flat-out rejected, you now know there is nothing you can possibly do to make him like you that way. So let that lighten the load. He’s just a guy. A nice guy, I’m sure…but just a guy. You got on in the world fabulously before you ever knew he existed, and you’ll live a fantastic life from now on after knowing him too.
Make some headspace for someone to try asking YOU out. You’ve done your bit for forward-thinking women and equality in the dating world by now. Let the fellas shit themselves for once. The ones who DO fancy you will get shit done!
Best of Luck! I’m off to get this entire message tattooed on my own forehead… 🙂