He has to put his cellphone on speaker while he tried to plunge the barrel of heroin into her neck.
In the six-degree Celsius cold, the rest of her veins have flattened, and the plump vessels in her neck are the best bet.
But something was stuck in the needle and no matter how how hard he tried, he couldn't get the drug into her system.
"Did you filter it?" "Small Paul" asks the 27-year-old woman.
She was unsure, so he pulls out the needle and starts over. She's a friend, he explains, and needs his help to do this.
He tells her that pushing a solid clump of heroin into her bloodstream might not have a happy ending.
"The heart valves are very delicate, they're not made to pump solids," Paul tells her, adding it could cause a stroke.
This is one bit of drama playing out in the early afternoon at 106 Avenue and 135A Street on Thursday in a park now occupied with about 10 tents and the homeless who now call it home.
Many don't like going to the cold and wet weather shelters.
Paul's 42-year-old girlfriend says the facilities are available, but she doesn't think they're safe.
She's trying to get off methadone, a drug used to take the edge off heroin withdrawal.
Ironically, she's using small amounts of heroin (chipping) to get herself off methadone.
She believes in about a week's time, she and Paul can get clean and sober and get on with the lives they were supposed to have.
This impromptu injection site isn't a welcome feature for many of the businesses in the Whalley area.
Pete Nichols, owner of Whalley Printers, says just prior the election, civic officials stopped trying to clear the property of the small tent city, perhaps due to the bad optics of ousting homeless people.
But the impact on local businesses has been huge, he says.
"I'm picking up needles," Nichols says Thursday. "It's a pretty tough street."
Anything left unsecured in the area is quickly stolen, Nichols says.
He says the tent city has been up for months and city hall has done nothing about it.
"There was even a guy with a small mobile trailer that would pull in there and stay a week," Nichols says.
But options aren't that great, Paul says.
He was kicked out of the Front Room drop in centre for a week after hitting another guy with a laundry bag, in what he describes as "horse play."
Either he finds some shelter – namely his tent – or he'll freeze.
He and his girlfriend both want a permanent home, not a temporary shelter.
Meanwhile, he agrees with Nichols – it's become a pretty tough street.
There's a guy who's been stealing drugs from the people living in the tent city, Paul says.
"There's a reward if I smash him out."
Paul is 6'2" and 230 pounds, but says the thief is big too, and well built.
Paul's girlfriend is hoping they'll be off the streets soon. She wants her five-year-old son back and wants to get back to her job as a professional nurse.
She knows that will take time.
Clean time.
Shortly after the conversation begins with a reporter, Paul's phone goes dead.
Attempts to call him again fail.