Judges 16:16 (NKJV): And it came to pass, when she (Delilah) pestered him (Samson) daily with her words and pressed him, so that his soul was vexed to death...
There are many things one can learn from Samson's life experiences and mistakes, and I believe nothing is written in the Bible without a purpose (or reason). His story might be a tragic one, but at least he did fulfil his calling in the end (Judges 16:23-31).
Samson was to be a son of rest because His father's name, Manoah (Judges 13:2) means 'man of rest, quietness, being settled' in Hebrew. The word 'Manoah' here is of the same word as 'Noah' ('Nuwach' in Hebrew), which also means 'rest, quietness, being settled'. You see, only a son of rest (like Noah) could build his Father an ark! (Genesis 5:29)
Note: When I write about 'rest' here, I'm referring to one's inner rest, and not so much about one's physical rest (though there is a place for this too).
'Building an ark' here simply speaks of 'building God's plan/blueprint'. In other words, it takes a son of rest to be able to fulfil God's 'plan/blueprint' effectively. For Samson, God's plan/blueprint for him was to deliver Israel out of the hand of the Philistines (Judges 13:5).
Even though he did have a weakness for women (and he couldn't control his lust for them), I believe the underlying reason for his downfall was due to his inner rest being taken away. This was the real secret of his strength, i.e. he 'being at rest' in the Lord. When one is at rest in the Lord, that's when His strength would also come and take over!
Of course, having said all the above, one also cannot deny that he (Samson) should have restrained himself from being enticed by harlots, and should have fled (from them) in the very first place. The Bible says 'to flee youthful lusts' (2 Timothy 2:22). This 'carelessness' on his part in turn opened a 'loophole' for the enemy to come in and take advantage of him, and it eventually led to his inner rest being robbed away!
Let me explain now from the Bible.
From Judges 16, you'd see that not until Samson's rest was being taken away did he get overpowered by the Philistines. And the woman in the thick of this whole thing was none other than Delilah (Judges 16:4). And the lords of the Philistines then came up to her (Delilah) and said to her, "Entice him, and find out where his great strength lies, and by what means we may overpower him, that we may bind him to afflict him; and every one of us will give you eleven hundred pieces of silver." (Judges 16:5) And Delilah did as they said (Judges 16:6-15). By the way, and interestingly, the name 'Delilah' in Hebrew means 'to drain someone of his rest, to exhaust someone of his energy, or to thin something out'!
Judges 16:16-17 then says, 'And it came to pass, when she (Delilah) pestered him (Samson) daily with her words and pressed him, so that his soul was vexed to death, that he told her all his heart, and said to her, "No razor has ever come upon my head, for I have been a Nazirite to God from my mother's womb. If I am shaven, then my strength will leave me, and I shall become weak, and be like any other man."'
The word 'vexed' here simply means 'being drained, distressed, or annoyed'. In other words, Samson was so 'drained' by Delilah that he eventually lost his inner rest. The Bible says he was being pestered daily with Delilah's words, and pressed hard, probably from every angle! And as a consequence, his soul grew so tired even to the point of death! And that's also when he told her all his heart's secret.
Judges 16:19 says, 'Then she (Delilah) lulled him (Samson) to sleep on her knees, and called for a man and had him shave off the seven locks of his head. Then she began to torment him, and his strength left him'. This speaks of Samson being cut off from his rest in the Lord. The number 'seven' in Hebrew means 'finished, perfect, completed work, or enter into rest'. For example, the Bible says 'six days God worked' (Genesis 1:31), 'on the seventh day, God ended His work which He had done, and He rested on the seventh day' (Genesis 2:2), and 'then God blessed the seventh day and sanctified it, because in it He rested from all His work' (Genesis 2:3).
Now, let's see what happened to Samson when he lost his 'seven locks' (i.e. rest) that eventually caused him to lose his strength (i.e. his authority and power). Judges 16:21 says, 'Then the Philistines took him (Samson) and put out (i.e. bore out) his eyes, and brought him down to Gaza (i.e. 'being treated harshly and roughly in a stronghold'). They bound him with bronze fetters, and he became a grinder in the prison'.
'Put out his eyes' here means 'losing his perspective and vision in life'. In other words, when God's people lose their rest in the Lord, they'll also lose God's perspective and vision for their lives. This may even lead to them being 'bound' and 'imprisoned' (i.e. 'taken captives') in the 'stronghold' of the enemies.
So, people of God, never allow anyone (or anything) to rob you of your rest in the Lord! When your heart (and soul) is at rest in the Lord, you'll be less likely to make any rash decisions that may cause you to regret later in your life. Guard your rest in Him and continue to stay in His rest! Also, when one is at rest, he/she can receive God's wisdom and revelation more clearly and accurately. In contrast, one cannot if he/she is anxious or in distress. The solution is to cast all your cares (and anxieties/worries) to the Lord, for He is the Lord who cares for you (1 Peter 5:7).
Today, as a believer in the New Covenant, you can find perfect rest in Christ because of all that He has already done for you on the cross. His work on the cross is already finished and completed. The Bible says 'be diligent to enter into this rest' (Hebrews 4:10-11), i.e. resting in the perfect work of Jesus Christ on the cross. Amen.
Note: Having written all the above, I would also like to end with this: Your God is also a God of second chance. Judges 16:22 says, 'However, the hair of his (Samson's) head began to grow again after it had been shaven'. And Samson found strength again (Judges 16:23-31). There's still hope, my friend, no matter what your mistakes may be in the past. Let the bygones be bygones, and begin to look to Him afresh and anew today. He's here for you, and His love (for you) never fails (1 Corinthians 13:8). Let this day be a new day and a new beginning for you as well, and I pray His strength be released upon you afresh and anew all over again. In Jesus' name. Amen.