At one of his lowest moments, X-Men's Wolverine admitted to being jealous of Daredevil and his luck with the ladies. Brainwashed into becoming the Hand's lethal assassin, Logan has the world on high alert due to his powers (like his healing factor), training and connections to some of the most powerful Marvel heroes. While SHIELD and the Fantastic Four put up quite a fight, Wolverine's hit list brings him to Matt Murdock's doorstep where he admits to himself that he doesn't understand what these women throughout the years see in the blind lawyer from Hell's Kitchen.
In the "Enemy of the State" storyline by Mark Millar and John Romita Jr, Wolverine is convinced to come to Japan to help a friend resolve a kidnapping gone wrong when he ends up walking into a trap. Despite slashing his way through mystical foot soldiers, Logan is beaten, killed, and resurrected by the Hand and their new partner, the Gorgon. Once in SHIELD custody after discovering his mutilated body, Wolverine and the others learn that he has been reprogrammed again to become an assassin, attacking specific individuals in hopes of assassinating and eventually recruiting them to join the Hand who're collaborating with Hydra. While SHIELD recruits Elektra due to her experience with the Hand, Wolverine infiltrates and attacks the Fantastic Four, continuing a coordinated and devastating rampage that concerns many of his former friends and allies.
In Wolverine #23, Logan cleverly uses an EMP to shut down power throughout central Manhattan, blanketing the city in darkness while Wolverine and a legion of Hand ninjas move diligently towards their next target, Matt Murdock. Aware of Matt's super-senses and knowing SHIELD would have its focus on others, Wolverine and his new allies get the drop on him, stating that Daredevil has been a desirable candidate for the Hand for some time now. In Wolverine #24, Elektra and SHIELD springs their own trap for Logan who considers Elektra's history with Matt Murdock and doesn't understand what her and the other women he's dated and slept with see in "the biggest himbo who ever wore a pair of tights after all."
When the Hand killed Wolverine, they took advantage of his nigh-immortality thanks to his mutant healing factor and use their blend of chemical and mystical conditioning to revive him on their terms, Logan fighting with an internal voice tapped into his dark feelings and impulses. When it comes to Daredevil, Wolverine agrees Matt's powers, training and most importantly, his history with the Hand would make him a perfect recruit. When Logan and his assassins are attacked by Elektra, he expresses jealousy and contempt over Elektra's protection of Matt despite them no longer being together. Although Logan has had his fair share of women throughout his long life, they often end up hating him, wanting to kill him or being unattainable. Although he's barely in control of this version of his worst self, it appears his feelings are genuine when he asks what Elektra or others like Karen Page see in this man who isn't rich, smart, or even funny.
While all hell breaks loose, Wolverine appears to take his mission to kill and convert Daredevil for the Hand personally, channeling his disdain for someone who ignores or rejects true love which has remained unattainable for Logan for a long time. Although it is later revealed that Elektra was the Hand's real target all along, it doesn't make Wolverine's jealousy over Daredevil's sex life any less funny or whimsical considering there's likely very little Matt was ever jealous about in Logan's life.