His long hair was left loose but his beard was tied into a pony tail! He was wearing long, baggy shorts, had blue eyes, and a big smile when he walked into the Kotel.
"Hi, where're you from?"
"You look it." (Referring to the hippie days)
"What are you doing in Israel?"
"Traveling with my girl friend. She's over there." He pointed to the women's side. "She's Jewish."
(Uh, oh! Not my favorite job to tell a non-Jewish man that he should not be with his Jewish girlfriend)
"Anyone in your family Jewish?"
"Yeah, my mother. She's the only one."
"Are you sure she's Jewish?"
"Yeah, we all know it."
"Well, if your mother is Jewish then you are Jewish. Come, I'll take your Jewish blood pressure."
"What are these?"
As I put the tefillin on him I explained that tefillin are a sign that we will do what Hashem wants us to do and we will think about what Hashem wants us to think about. He read the Shema in English and I showed him how to share the mitzvah with his loved ones by praying for them.
"You're Jewish so you have to marry a Jewish girl."
"Yeah, she's right over there."
"Go to a local Chabad rabbi so the wedding will be proper, and the babies will be born with that spiritual advantage."
For his whole life he thought he was a gentile. He walked into the Kotel area as a stranger visiting the Jewish land. He had a Jewish girlfriend but he himself was an outsider. Then all of a sudden he found out that this Holy Land is actually his land too… and best of all (at least in his eyes) the girl he loved was really for him. A very happy day.