A paramedic asked a colleague to take a picture of him for Snapchat - and dropped his underwear for the shot, a tribunal heard.
During the shift on October 25, 2013 he added: 'If you were in a bar and I came in and said would you go out with me, would you?'
After the shift Woodland asked her to come to the locker room take a picture of him to send to another co-worker, Georgia King, through Snapchat.
When she came into the room Woodland was stood with his underwear around his ankles, a Health and Care Professions Council investigating the incident heard this week.
Ms Hannah Eales, for the HCPC, said: "Mr Woodland's conduct fell far below the standards expected of a paramedic."
Stuart Critchin, who carried out the subsequent investigation into the incident, described how Woodland was chosen to supervise as she was having difficulties with her mentor.
They were not getting along due to a "clash of personalities" and she was also "struggling in her own processes".
"It was decided that Mr Woodland would work a shift with her to see how she was, how she was doing and to offer her some mentorship," he said.
During the shift a number of inappropriate comments were made by Woodland, who told the colleague: "I thought you were pretty."
Woodland then described sending a Snapchat picture to Miss King of himself smiling.
The colleague suggested that he pull a "muscle man" pose instead and when they returned from their shift at about 8pm Woodland asked her if she would take the picture of him.
He led her to the back of the station to a portacabin which served as an overflow locker room where he started to take his shirt off so as to 'hide his badge'.
As the woman was setting up phone for the snap, Woodland turned to face her with his trousers around his ankles.
She put the phone down and walked away after taking the picture and sent a text to Miss King immediately to warn her of the picture she was about to receive.
Then in February 2014, Miss King was assigned to work with Woodland but did not feel comfortable with him and told bosses what had happened.
When Woodland was interviewed he said he could not remember the incident.
Woodland, who was not present or represented at the hearing, denied all the allegations against him in a statement submitted to the panel.
If the allegations are proved on the balance of probabilities, Woodland could face being struck off.
The hearing in Kenington which began on Wednesday continues.