Advice sought with regards to nasty evil emotional problem

A friend of mine posted this problem to me. After dwelling on it for quite some time, I am unable to come up with a satisfatory answer or course of action, so now I seek enlightenment from the Sages of SDMB.

The situation is as follows:

The question is then, what should he do? Should him help her to forget the past, thus giving up whatever slim chance he still may have? Or should he let things be, cringing at the thoughts of Yvonne suffering from being gnawed from inside, thus being rather immoral, but will be better (according to him) in the long run?

What do you think, Dopers? All responses are welcome, including whether you think Howard was right about Yvonne on that fateful night in 1998.

My opinions:

  1. She may have been flirting with him in 1998. Since he was interested in her, he should have absolutely made a move to see where things went. Waiting for a flashing neon sign guaranteeing 0% chance of rejection or risk is a good way to miss a lot of opportunities, as he has hopefully figured out by now.

  2. I think the part about helping Yvonne get over her ex-boyfriend is a load of crap. He seems to think he can control whether or not she’s unhappy about a past heartbreak, which is insane. It’s not his job to fix her emotionally, regardless of whether they’re dating or just friends.

  3. If he wants to date her and thinks she’d be happier with him than Vincent, he should grow some balls and ask her out. Chances of rejection are pretty good, since their relationship has almost certainly solidifed into platonic friendship, but it doesn’t sound like he’s happy just being friends with this woman, so he might as well try for what he actually wants.

Really, I think he should stop hanging around with her and go find someone to date. Obsessing about incidental contact five freaking years ago is sad. He obviously doesn’t think of her as just a friend, so he needs some distance from her in order to focus on dating other people. Maybe in the future they can be friends, or even date, but for now, they should stay away.

Any other thoughts? :slight_smile:

I think that Giraffe hit the nail on the head.

He wasn’t so tactful about it, but then the truth is rarely ever tactful.

I think Giraffe pretty much got it. Especially the obsessing over the touching - it’s quite possible that either she’d been drinking a little and so was a bit more relaxed than normal, or that some ex of hers was there (or someone else she wanted to make jealous). Either is quite likely.

He has to either let her go romance-wise, or just suck it up and ask her out.

Snooze, ya’ lose. Howard snoozed in '98 and lost. “Faint heart never won fair lady” or something like that.

Thanks, Giraffe for giving an accurate in-depth analysis so I can be flippant.

Final thought: If Howard’s been worried about the incident you described for Five Years, he needs some professional help. Two very different professions come to mind…

Here’s a thought - why doesn’t Howard send the lady an invitation for a date?

At that point, she can say yes, or no, or ignore him.