Gabriel Conroy is really too self-centered to have any kind of meaningful relationship with a woman. He's a man who likes to be in control of things, and he sees women as somehow getting in the way of that objective. Gabriel is happy to romanticize women, according them a mythical role in Irish culture and society. But the thing about a mythical role is that, by its very nature, it isn't real. And it's perfectly clear that Gabriel doesn't see women as anything like equal partners in the real-life Ireland he wants to see established.

Gabriel illustrates his generally disrespectful attitude toward women in his treatment of Lily. After his forced attempts at flirtation with her fail miserably, Gabriel tries to retrieve an embarrassing situation by thrusting a coin into Lily's hand. In this way, he is reasserting both his masculinity and his social status, thus placing Lily in a subordinate position.

Gabriel is so self-absorbed, looking at the world through the lenses of his own needs and desires, that he is constantly misunderstanding and striking the wrong note with women. He is condescending, as when he asks the maid Lily if she is out of school, and when she says yes, replies that she will no doubt marry soon. This annoys, rather than pleases, Lily, who says men are all after only one thing.

Later, Gabriel makes a comment that is supposed to be a joke but could easily be interpreted as an insult when he says that:

It is not the first time that we have been the recipients—or perhaps, I had better say, the victims—of the hospitality of certain good ladies.

He interprets the ladies in question as turning red "with pleasure," but a reader could also interpret their "crimson" faces as expressing anger at his passive-aggressive dig about people being their "victims."

Gabriel's worst blunder, however, comes after the party. He is feeling amorous towards his wife and is stunned to discover she is not thinking of him at all, but of her dead first love, Michael Furey, a person he never dreamed existed. It angers him that his wife could have loved someone other than him or have had a life apart from him. He understands their disconnect when he thinks:

While he had been full of memories of their secret life together, full of tenderness and joy and desire, she had been comparing him in her mind with another.

Of course, she may very well not have been thinking of him at all, but that idea seems to be beyond Gabriel's comprehension. Whatever the case, he has a hard time relating to women, even his wife.

Gabriel Conroy singularly distinguishes himself by showing that he has no idea in how to relate to women. First of all we have his incredibly embarrassing faux pas of trying to make small talk with Lily and then hoping to give her a tip for Christmas but being left in the rather awkward situation of having to run after her to thrust this rather unwelcome attempt to be munificent upon her. Secondly, he is easily bettered in a battle of verbal wits with the indominitable Miss Ivors, and lastly, he desires an amorous encounter with his wife but remains completely unsure about how to go about it, and is left only to imagine what he would like to occur:

Her would call her softly:

--Gretta!

Perhaps she would not hear at once: she would be undressing. Then something in his voice would strike her. She would turn and look at him...

Gabriel's inability to relate to women is shown above all in his own relationship with his wife. Planning to seduce her, he is left facing the reality of the fact that he is only knowledgeable about such matters in his own imagination. He is a perfect Joycean hero in his dis-ease and inability to act.