Kayla Rosenfeld found herself probing intimate details of a stranger’s life Monday.

“Do you like girls?” she asked a homeless man in an effort to record his sexual preference. After questions about his race, Rosenfeld asked about his gender identity.

“It was awkward,” she said afterward. “It sounds like a completely ridiculous question … to somebody who appears to be in their late 50’s, 60s, to ask, ‘Were you born a man?’”

Rosenfeld spent her day off surveying homeless people in Wahiawa for the annual point-in-time count of Hawaii’s homeless population, conducted largely by volunteers. Despite uncomfortable, moments, Rosenfeld said she was happy to be one of about 40 volunteers who gathered for the first day of the week-long effort to collect data on Hawaii’s homeless population.

Natanya Friedheim/ Civil Beat

Wahiawa-based nonprofit ALEA Bridge organized the count for central Oahu and the North Shore.

After four hours of surveying in ditches, parks and sidewalks, Rosenfeld and other Wahiawa volunteers met at a church to debrief with ALEA Bridge Director Phil Acosta. He acknowledged the challenges faced by volunteers.

“It is very intrusive,” Acosta said of the survey questions. “We do have to make some effort to ask the question, even if it’s awkward.”

The data helps nonprofits and lawmakers measure the success of their homeless programs and understand the populations they serve.

The survey, a federal mandate, is by no means perfect.

It helped that one of ALEA Bridge’s volunteers, Joey Bagasol, speaks Illocano and Tagalog, the languages spoken by many Filipino immigrants to Hawaii.

“When they start speaking their own language, they’re more comfortable,” Bagasol said.

Natanya Friedheim/ Civil Beat

Volunteers put on neon yellow T-shirts before splitting up into groups of about 10 and venturing to different pockets of Wahiawa.

When one group fanned out around a homeless camp near Lake Wilson, it was difficult to know who should approach the homeless and who should hang back.

Being approached by a group of 10 eager surveyors might be overwhelming.

“The key with the volunteers is to make sure the homeless aren’t inundated with people,” said Cora Rada, an outreach worker for ALEA Bridge who led one group of volunteers.

Still, Rada said that outreach workers don’t have the manpower to do the count on their own.

Diane Nishijima and her husband were thwarted in their attempt to survey a man near Melemanu Park between Mililani and Wahiawa because their efforts coincided with a state Department of Transportation homeless sweep in the area.

“We didn’t really get to interview him because he was rushing to gather his personal stuff,” Nishijima said.

Natanya Friedheim/ Civil Beat

If volunteers miss someone, they write down a description of the person and place, and someone from ALEA Bridge will return the following day. The organization’s outreach workers already know many of the homeless in the area.

One challenge is that it’s not always clear who’s homeless.

Rosenfeld’s group walked passed a man riding his bike slowly down the sidewalk.

His clean blue jeans, sneakers and the vest over his T-shirt showed no signs of wear and tear, but a volunteer at the end of the procession stopped to ask if he was homeless. The two spent the next five minutes filling out the point-in-time survey.

The surveys only three to five minutes to complete, but a lot volunteers spend more time talking story with the people afterward.

One group in Wahiawa listened to a woman who cried as she talked about her life for 45 minutes. A volunteer at the meeting afterward said it was the most meaningful thing she’d done all day.

Another recommended the surveyors carry tissues to offer in case people start crying.

Jen Stasch is the director of Partners In Care, a coalition of nonprofits that organizes the survey for Oahu. Stasch describes the count is a rare opportunity for people in the community to get involved in Hawaii’s homeless crisis.

“Most people stand by helpless going, ‘What do I do? How do I help? How do I even formulate a solution?’ Well here’s one way you can help, get involved in point-in-time, help us collect the data,” she said.