The Angel Of Hell's Kitchen

Just with his dealings with Karen there’s:

His making out with her in front of Natasha

Thinking that the best time to confess that he was Daredevil was at her father’s funeral

Hell hitting on her while posing as his twin brother in general

Cheating on her with Mary

Throwing her history as a drug addled sex worker in her face (Yes, he threw the fact that she’d been taken advantage of in a huge way in her face. While they were under the impression that she’d contracted AIDS might I add)

And probably a few other things that didn’t immediately come to mind.

Yeah she gave him up for a drug fix, but he wasn’t always great to her either. And Guardian Devil even started with the reveal that she’d left him to take up a job in Los Angeles, in part because of their issues, citing that he tends to have trouble forgetting, even when he opts to forgive. Though she also cited that she felt she was becoming too dependent on him to fix her problems for her, which is another talk in general.

Then there’s him with his other girlfriends.

Natasha left him because she didn’t care for how he treated her. Just in general being a cad and undermining her because she was a woman if memory serves right. (Even in the 70′s she didn’t care to take that shit)

Cheated on his catatonic wife with Dakota

Mind wiped Kirsten and then broke up with her

His relationship with Heather in general, but let’s not forget that a few callous and thoughtless remarks on his part were the straw that broke the camel’s back that led directly to her death.

In short, yeah, he’s got a history of being not so great with women, whether he’s consciously aware of it or no.