I think he could have
>Herdier (boney)
>Sunflora (sunflowers)
>Zweilous (he has a twin brother he dead though)
>Tyrantrum (the dragos)
>Espeon (it's a psychic type and evolves though friendship, y'know, because PK Love)
>Type: Null (the chimeras)
Those are the ones I think would fit best, but other possibilities are Delphox, Vivillon, Bisharp, Cubone, Pignite or Vanillite because of his ice cream hair