I'm going to try and fit this within the space required, but my friend Steve at age 29 has never had a girlfriend before (or has had sex for that matter) and I feel he may have taken the wrong steps to resolve this.
Steve recently met a 37-year-old woman who he has nothing in common with and doesn't find her physically attractive, but is basically seeing her because she likes him (A key component Steve seems to be missing in most of the women he is attracted to is they never seem to be attracted to him) and he is tired of being lonely in a romantic sense. As a result, both his friends and family have seen him suffer.
The woman has four kids, the oldest who is 18 and also has birthed a child herself. Most of the time Steve spends with her almost always involves the kids tagging along, which he says he finds very challenging to deal with as they seem to be delinquents. The two oldest of the four also make fun of and insult Steve, which he says makes him not want to associate with this woman. He showed me photos of her, and what caught my eyes was how messy her house was in the background of the photos, Cheetos on the floor, toys all over the place, and garbage bags waiting to be taken out. Steve recently brought her to a family reunion, and I basically heard from him the woman embarrassed him there by being belligerently drunk, which is made worse considering most of Steve's extended family do not drink and don't take too well at all to drunkenness. We are unsure if she is employed, she says she is a "domestic engineer" but most of her time seems to be spent at home looking after her children (and one grand child).
Steve says he finds her annoying, he isn't interested in her activities and interests, and I'm not even sure if he's had sex with her yet. However, she seems to let him get close in terms of a romance and he can "open up with her and get intimate", something he's never been able to do with most of the women that have crossed his life since they all seem to be uninterested in him. Worst of all, the woman has begun asking Steve for money so I, his family, and friends are beginning to worry not only is she beginning to drain him emotionally, but possibly financially.
The best possible outcome is I want to help Steve find someone who not only he likes but likes him back also. The problem is having known Steve for years, he seems to have many problems with women romantically. As aforementioned, most women don't seem to be interested in him and he seems to be rejected a lot, some having accused him of being a creep. I think including this woman, only four I can count off the top of my head have actually been interested in him, and none of them he has been interested in. Like this woman, they all seems to have serious issues (i.e. heavy drug use).
On the other hand, I almost want to let Steve stay with this woman as a result of his problems with women, these few women that are interested in him (albeit he isn't into them) seem to be very far and few in between, as an example there was a time where there were eight years between him finding the next girl that liked him. As such, I worry that if Steve lets go of this woman, he'll be tormented with years of romantic loneliness again.
I'm basically trying to pick the lesser of the evils here, that is Steve being lonely though free of a bad relationship (Plus also having what seems to be a slim opportunity of finding someone compatible with him) or seeing him in a relationship that is draining and tormenting him, though at the very least he has someone he can deeply confide into, something he claims he cannot do with a platonic friend.
The optimal solution I feel is for Steve to dump this woman while trying to find ways for him to appeal to more women in hopes he finds someone that he can have a good relationship with. How do you think I, the rest of his friends, and family can help him?