Heh - you guys have reminded me that my husband’s 14 year old cat was originally picked out by his live-in girlfriend at the time. When they split up, he inherited the cat in spite of his allergies because the cat had decided he was her human (you only have to see them together once to know that this is utterly true - she adores him). I love this kittie now, too - it doesn’t matter to me how she came into his life.
I know this isn’t what you mean, but I’m picturing the painting now with a big, red, drippy painted “X” over the ex. 
I am a pretty jealous person by nature, but I wouldn’t have a problem with this picture, as long as it wasn’t given a special place of honor in the house, and you weren’t sneaking late-night phone calls to her and having lunch frequently or anything. And I’m not giving back the diamond earrings I once got from a boyfriend, and you can’t make me.
I would actually think it was lovely that you were sane and rational enough to be able to keep a picture with your ex in it without developing any weird emotional baggage about it. The rules for pictures of exes are as follows:
Do keep any pictures from:
-weddings
-family events
-pictures with more than the two of you in them
-anything with above average sentimental value (like your painting)
Do not keep:
- headshots of your ex
-beaver shots or other nudes
-pictures upon which you drew moustaches and devil horns to show how evil she is
-anything else that might indicate you are not quite over the whole situation.
But…what if it’s some of my best work? I’m a picture defacer from way back (not necessarily of exes) - blacked-out tooth, eyeglasses and horns are my trademark.
I know from experience that a painting depicting you with an arm around an ex-flame, no matter how tasteful and innocently portrayed, will bring you nothing but frequent and extreme acts of passive aggressiveness from any and all current or future lovers who view the painting in question. There is only one solution if you want to continue to date women and keep your painting, while maintaining its high standard of quality and artistic symmetry (i.e. simply painting your ex out of the picture breaks the symmetry, creating what we artists call arty discombobulation).
You need to contract with the original painter, the former aunt-in-law, and have her artistically “morph” the ex into something far less emotionally explosive. If she is as talented a painter as you say, she will use her artistic “eye” to determine exactly what to morph the ex into, keeping the same “feel”, the same visual impact, maintaining symmetry and most importantly, using the least amount of paint. For example, if your ex has big feet and a little head, the painter may wish to brush stroke her into a kangaroo; if she’s a large-ish woman with a big aquiline nose, she could easily be turned into a rhinoceros; Big teeth and wearing a brown coat?—grizzly bear! Bottom line: keep dating, keep the painting, change the ex. 
You inspired me to start a new thread, pbbth.
ETA: A kangaroo or a bear is even better than a big red “X”, Tibbytoes. 
That’s you? I’ve always admired your work!
I think I’d spin it a bit - “oh, a very dear friend painted that for me. I just love New York.” That sort of thing. If the relationship’s new and you’re worried about the new gal’s reaction, no need to tell her yet who the figures in the picture are. Or your relationship to the painter.
I think there’d be time later to tell her the whole story, provided you chose the right time, place, and tone.
However, I’m not a particularly jealous person. All women are different, though, so this course of action might not be the best one.
Thank you. I’ve been practicing many years now.
I wouldn’t have feelings about it either way, but I’m from a family of artists and dated a lot of artists, so there’s always a nice portrait of somebody around.
Yes the Aunt is “her” aunt, not mine.
Thanks for all the responses. Basically I guess how ‘she’ reacts will just tell me about her and I shouldn’t worry about it.
If my camera wasn’t on the fritz I’d post an image of it.
It never would have occurred to me that this kind of thing would be an issue for anyone. Perhaps you all could give me your opinion about how you would react to my painting(s).
Hanging in a very prominent place in my apartment is a lovely watercolor landscape by my ex-mother-in-law. She’s also a professional painter who’s works sell for goodly sums. It was a Christmas gift to my ex and I, and a very generous one at that, given what her paintings sell for. When we divorced, I asked if I could have it, as I sure can’t afford to buy one! Fortunately, he said yes. If anybody asks about it, I, without hesitation, tell them it’s by my ex-mother-in-law and brag about what a good painter she is.
Would this bother any of you?
And to add to it–I have three other pieces by her. They’re unfinished paintings that she felt weren’t quite up to snuff so she didn’t want to sell them. When she gave them to me, she made me promise that I’d never represent them as being indicative of the quality of her real work! 
But they’re pretty and I’m going to frame them and hang them in the kitchen or something.
Would you be more bothered if I had 4 paintings by her hanging in my home?
That wouldn’t bother me. The only thing that would bother me about the OP’s painting is the fact that his ex is actually in it. I am trying to imagine myself being okay with a painting of my boyfriend together with his ex hanging in our living room, and I have failed miserably.
My boyfriend feels uncomfortable with me wearing jewelry given to me by my exes. The jewelry I have has no sentimental meaning whatsoever to me, so I don’t think it’s that big a deal, but I also think that his feelings aren’t unreasonable and I love him more than I care about the jewelry, so I don’t wear it. It’s not a big deal. I feel the painting is something similar. It may not have any sentimental value to the OP, but if it bothers his hypothetical girlfriend, is it worth making a fuss over?
ETA: Of course, it may not bother her at all. I’m just saying that IF it does, and she’s being reasonable about it rather than hysterical, I’d think it reasonable to have the painting removed, at least from her sight.
Another vote for keeping it where it is.
Especially since you really can’t tell who the couple is in the painting. If a date / girlfriend asks more about the work, tell her. If there are issues at that point, a move to another place (less prominent, your office, etc ) might be prudent. If there are still issues, you might just want to rethink the relationship with that particular woman.
I’d think it was a really neat momento, but I’d wait to explain until it came up naturally, at a time where you can point proudly to it and explain it’s history; it IS genuinely neat.
This wouldn’t bother me in the slightest. In fact, if one of my friends told me she was upset because her boyfriend had such a painting, I would think she was being extremely dramatic about things.
It’s a nice piece of well made art and it has some sentimental value. Just because you previously dated another woman doesn’t mean you should now remove everything that may be in some way related to her from your life. Especially since it is a street scene - I assume adding you two into the picture was just a nice touch rather than the main focus. Now if you had a nude painting of the two of you in a passionate embrace, that would make me a bit uncomfortable. But I still wouldn’t insist you got rid of it, if, like you say, it has merit as art in it’s own right.
Also, I wouldn’t mind when you told me about it. Don’t go into it with the attitude that it’s a dirty secret you need to confess. It isn’t. You’re not telling her that you have a criminal record for drugs trafficking or that you have genital herpes. It’s a nice story. I’d love someone to do that for me, so I wouldn’t blame you for wanting to keep it.
If she comments on the painting, tell her the story. If not, don’t. Don’t make a big deal out of it.
Hang it over the bed and say ‘Sweet dreams’ to it every night. The have an artist friend stop by every day while the girlfriend is out and add a little dab of paint, so the figure of your ex seems to be turning to face the viewer a little more each day. Hilarity will ensue. I swear.
Well, if the new girfriend really doesn’t like it, you could always commission a painting of yourself as a centaur to replace it. Chicks dig that.
We all have pasts. It’s how you bring it up that determines how it goes. It could be a nice gateway to the inevitable “my past” discussion.