You must first have both met and defeated your rival in Mt.Moon (Whose Pokemon are in their high 40's and His start being Lv.50.)
Once doing so. He will declare that his training will continue in the Dragon's Den. It is there where you can talk to him (You must first fly to Blackthorn City and then Surf into Dragon's Den, Surfing into the shrine [which you'll need Whirlpool also for] to talk to him)
Once you've triggered the event, Lance and Clair will team up and fighting against you and your rival.
This is the only time you will be able to battle alongside again. After this, On Tuesday's and Thursday's he'll be there training.
You're able to rematch him once every Monday and Wednesday.
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Yeah you do. At the dragons den you and your rival battle both Clair and Lance in a double battle.
Once you've met your rival at mount moon, go to the dragons den. There you will have a double battle with your rival against Lance and Clair.
You get to double battle Lance and Clair in the Dragon's Den after you have defeated your Rival in Mt. Moon.
Go to the Dragon's Den on Mondays or Wednesdays, where you will see your rival. He'll talk for a bit, and afterwards, Lance and Clair will show up and engage you and your rival in a double battle.
you go out of Dragon's Den (if its Friday)then you see Clair by the bridge in Friday Mornings.You talk to her then she will give you your phone number.