Pride leads a person to do things and take risks a humble person would not take. Pride in life leads to presumption; I won’t fall off this bridge … I won’t get a sexual disease; spiritual pride leads to grievous sin. Instead of fleeing sin, pride plays with sin.
Samson lived physically and spiritually dangerously, symptomatic of pride. He disregarded his Nazirite vow, flaunted God’s grace and gifting, and dismissed the danger of personal sin. The Bible warns us to take heed lest we fall (1 Cor 10:12).

I. Samson Loved (Judg 16:4-5). This is the first mention of Samson loving a woman; yet the only woman who loved Samson was his mother. There’s nothing wrong with loving a woman unless she’s the wrong woman.
None of Samson’s relationships were as he expected. He always did what was right in his own eyes, not God’s. Samson loved Delilah, whose name means flirtatious one. She wanted Samson for financial security, Samson desired love; both used each other for personal gain and that’s not love.
Philistia had five major cities and each city leaders offered Delilah 1,100 shekels of silver each (worth $269,000 USD). In exchange for payment, the Philistine leaders demanded she entice (seduce, make a fool) Samson and learn (1) the secret of his strength (so it wasn’t obvious muscles), and (2) how to subdue him so they may torture him.

II. Delilah Deceived (Judg 16:6-19). Delilah and Samson had four exchanges about his strength. Each time, Samson knew the woman he loved was working with the Philistine captors hiding in the room each time; he said, If they bind me (Judg 16:7, 11).
We have the proverb, Fool me once shame on you; fool me twice, shame on me. So how was Samson so blind to what Delilah was doing? Pride. Pride made it easier for Samson to believe Delilah’s love lie than the truth about their relationship. A proud heart refuses to look at, accept, or believe the truth. It not only rebels against truth, pride denies, defies, and dismisses truth. Pride caused him to believe he could do anything (like Satan and false believers, Is 14:12-15; 2 Pet 2:4-6; 3:5-9), so he took unnecessary and dangerous risks, presuming upon the gracious protection and presence of God.
Delilah rightly accused Samson of mocking and lying to her. She said that if he really loved her he would tell the truth (Judg 14:16-17). Little did she know, but each answer got closer to the truth and each time she took him at his word, he escaped from the snare. Samson knew he couldn’t trust Delilah, yet his ego kept him with her; Delilah knew she couldn’t trust Samson, but money kept her with him.
After three failed attempts to get the truth from Samson, Delilah changed tactics and pestered (pressured, nagged) and pressed (persistently harass) him day by day until his soul was vexed to death. She wore him down with manipulating tears. Samson revealed the truth, not because he loved her, but she wore him down. He gave up and gave in, revealing what would make him like any other man. He fought against being God’s man to deliver Israel to be like every other man. Too often we want to be like every other man instead of the Man, Christ Jesus.

III. Samson Defeated (Judg 16:20). Samson’s soul was worn down by a woman, but not by his sin against God. When he awoke from his slumber, Samson presumed upon the Lord’s presence, not discerning that the Lord had departed from him (Judg 16:20; 1 Sam 4:21).
The secret to Samson’s strength wasn’t his long hair. His strength came from the presence of God, not the sign of his vow. His faith wasn’t in God, but the external evidence of the vow he neglected. He believed he was God’s man and could do as he wished. He presumed upon the grace of God.
Grace upon grace, yet Samson, like Israel, lived beyond grace. Both became settled in their relationship with God and took Him for granted rather than be grateful to Him.