Maybe. Maybe not. But as far as scripture revealing that as established fact — I don’t think so. I haven’t found any scripture that specifically puts Him in the vicinity of one.
It’s just that we’ve heard this phrase so much that we’ve tended to accept it as fact, and it might not be. (People tend to do that with things they’ve heard over and over.)
In Matthew 25:6-13 and in Mark 14:1-11, Jesus is dining at the home of Simon the Leper (presumably cured, but there is no record of it) at his invitation when a woman anoints Him with expensive perfume. No slur is made on her character sexually; the charge against her is that she wasted the perfume, which Jesus refutes. In a similar record in Luke 7:36-50 (where the host is identified as a Pharisee, also named Simon), and all that he says to himself is “If this man were a prophet, he would know who is touching him and what kind of woman she is—that she is a sinner” (v.39). Jesus agrees that her sins are many, but that “her many sins have been forgiven” (v. 47b). Nothing is said about the nature of these sins. John 11:8 identifies her as Mary, one of the sisters of Lazarus; and chapter 12 relates the story with no comment on her character or sins.
The Samaritan woman He meets near Sychar at Jacob’s well in John 4 has been married five times and is living with someone she is not married to (vs. 17-18). Jesus, who has intuited this, says nothing about her asking for or receiving money for sexual services. It’s possible, but He seems to be very discreet in the way He phrases this revelation. (Almost as if He is not judging her, one might conclude.)
A woman who touches His garment in Luke 8:40-48 has a bleeding disease that undoubtedly troubles her reproductive system, but no inference can be drawn about its nature or source — certainly nothing that requires it to have resulted from illicit sexual activity.
The woman who begs Jesus to heal her daughter is simply described as foreign in Mark 7:24-30.
Finally, in the disputed passage beginning John 8, a woman about to be stoned or spared at Jesus’ word is described simply as “caught in the act of adultery.” Again, no exchange of currency for service is mentioned or implied.
If there are other instances of contact between Jesus and women of tarnished reputation, I’d still need to be convinced that the label “hooker” is deserved. If they didn’t sell themselves, they weren’t prostitutes. If we’re going to be pejorative, then the accurate term would be “sluts.” Is there really a need to be pejorative? We don’t pick on other sins like this one and say “Jesus hung out with pimps” or “Jesus hung out with child molesters” or “Jesus hung out with tax cheats” or “Jesus hung out with slanderers” in the absence of any scriptural evidence for it.
We know Jesus hung out with a tax collector/collaborator, a member of a revolutionary sect, a boatful of fishermen, and a traitor who became an accomplice to His murder. He dined at the homes of Pharisees as well as tax collector/collaborators and ate out with thousands at a time, even providing the food. He went to a wedding once where way too much wine was served, and He was the reason for it.
People of all sorts sought company with Jesus. They were all sinners. That was the big accusation of the Pharisees and teachers of the law in Luke 15:2: “This man welcomes sinners and eats with them.” (As if they weren’t sinners themselves … just as we are.) And they were right. However, there’s rarely any indication that Jesus actively sought these contacts — or that He shied away from them, judged, or failed to engage them as people loved by God. Point is, He was Jesus. He didn’t have to. They came looking for Him.
So I’d advise caution about repeating the phrase in the title or anything substantially similar to it as historical fact. It’s not strictly biblical. While it may convey Jesus’ loving nature and willingness to reach out to (and associate with) all of us who sin, it’s really not accurate to infer from scripture or imply to others that Jesus frequented dens of iniquity while His sandaled feet traveled Israel, Galilee, Samaria and the environs.
Would Jesus hang out with hookers — or any other kind of sinner one might care to single out — then or now? Without a doubt!
In fact, He does so almost all the time. His Holy Spirit within the lives of His servants reaches out in ministries to the homeless, the hungry, the incarcerated, the addicted, the poor, the rich, the self-righteous and the self-doubting. He is in His servants and they are in Him, doing the work God has prepared for them to do.
Jesus began it. We are to continue it. That’s what matters.