PokéBase - Pokémon Q&A
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I ask because:

Well, fairly recently, I noticed something...peculiar...while I was battling with my female Sylveon. Sylveon had just become infatuated with another Pokemon in battle after it used "Attract"

Now, at this point I used the move "Draining Kiss". It hits despite being Infatuated..and then hits again..and again for the KO! Three times in a row through infatuation!

That's fair enough, and I realize it could just be luck, so I decided to test it by battling online Via BattleSpot. After a while, I managed to get a Jolteon to infatuate my Sylveon. I used Draining Kiss, and guess what? Hit & hit through infatuation AGAIN!

This really makes me ponder...what if..Draining Kiss does indeed have a higher chance to hit during infatuation? If so, do other "Kiss" moves also have a higher chance to hit? Or was I just simply super-lucky?

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Nah it's just you mate. Such luck, much wow :3

Remember, Infatuation has a 50% chance of stopping you, so theres a decent chance that you'll be able to hit through it each time.
Draining Kiss has no description relating to anything with Infatuation or Infatuation having a correlation to Draining Kiss on any of the main information sites. There's also nothing on the web that I could find after a quick search correlating to it, and no one else really considering this a possiblity.

edited by
For sure lol. It's all in my head then.

..Would of been really cool if I had happend to discover something new though! I mean, it dose make sense how that might work. Lol
Don't see the point of your previous edit Indi. k fanks :3
He added a :3 lolol <(^.^<)