The 29-year old Scottish forward spent time on loan with the Seasiders last season, and in 2010, and now Holloway is keen to get him back to Bloomfield Road, perhaps on a permanent deal.
However, Holloway has his doubts about snapping up the £1million-rated Dobbie who has been performing well in pre-season under new Swans boss Michael Laudrup.
"I don't know whether we can get him back. We are playing Swansea and I might be able to talk to their manager while I am down there," Holloway told the Blackpool Gazette ahead of tonight's friendly between the clubs.
"But I am not that hopeful because he went and banged that hat-trick in the other week. That won't help my cause but it might help his."
He added: "All I've ever guaranteed (Stephen) is that I'll try to make him pickable for everyone else and I just love him.
"I wish I could go and wrap him up and bring him with me now but life isn't that easy, it doesn't work that way. And that isn't my chairman's fault, it's just life - he belongs to Swansea."