Dating Question: Can a Guy Be Too Nice?

Four ways that single men blow their chances with women and become friend material instead


Single women say they want the nice guy. But I'm not so sure. I recently had the following IM conversation with my friend Jill:
RICH (11:09:02 AM): punks, and rock stars
JILL (11:09:12 AM): pretty much
RICH (11:09:21 AM): hence Dave and you will never be together
JILL (11:09:27 AM): he's a good guy
RICH (11:09:30 AM): haha too clean cut and nice
JILL (11:09:35 AM): pretty much


Poor Dave! He's losing out to punks, bartenders, and rock stars! Nothing against these occupations (not that being a punk is an occupation), but the more important part of this conversation is that Jill stated that Dave (who adores her) is too nice.
A little more about Dave: He is well-off, takes care of Jill as a friend, and asks her to do fun things all the time... you know... dates? Imagine!
I had a friend who is now married who suffered from the "nice guy syndrome." On one occasion, we were standing in a bar and he announced that he had to walk five blocks to the subway station to pick up his date and walk her to the bar. We were none too pleased with this: Maybe we are not old-fashioned enough, but we figured if a girl makes it out of the New York subway, she should be capable (and independent) enough to walk five blocks to a bar.
His worst showing of being too nice was when he was on a first date with a girl and he walked her into the subway station (behind the turnstile -- he paid even though he wasn't riding the train) and waited with her for the train to come. When she stepped onto the train, he then ran along as the train was leaving, waving through the window at her until he couldn't keep up.
His gentlemanly strategy did not pay off. A few weeks later, I ran into her and they were no longer seeing one another. She joked about the train run-along and proceeded to hit on me. Was he too nice, or was she just a bad seed? Maybe a little bit of both.
Is it possible for a guy to be too nice? Here are some ways that this could ring true:
#1: He's So Nice, He Can Only Be a Friend
Hey, a good friend is hard to find. What sometimes happens when we get into a relationship? It eventually runs its course and ends, which means awkwardness and/or change in both of you, since you started off as friends. Maybe you can recover and remain buddies, but is it worth the risk if you find that you're really good friends with a nice guy? Also, sometimes the nice guy just has no edge, so he's destined to be just a friend.
#2: He's So Nice, He's Not Challenging Enough
I've recently learned from your comments: Women enjoy the thrill of the chase a bit too much. People like to wonder what's going to happen, that nerve-racking first few months when the "training wheels" are still on the relationship. And, no matter how much we try to deny it, we do like that we've won someone over instead of just having them give themselves up to us. If a guy is too easy, he may be ruining his chances.
#3: He's So Nice, He'll Always Be There
I've seen some friends take their time with a nice guy. Sometimes it works out, sometimes it doesn't. Maybe a woman wants to meet some new guys and "sow her wild oats" while the nice guy fawns over her. She enjoys keeping him in her life as a friend, but somewhere in the back of her mind she knows that she can probably return to him later. Again, it's all about risk management: If you want to take the risk of him meeting someone else, then go for it.
#4: He's TOO Nice, You Can't Trust Him
Sometimes people are so nice that it seems like they might have sinister overtones. I always see it on Lifetime movies: The guy comes into the woman's life and he is just perfect. Then he slowly disintegrates into a psycho freak. Perhaps a guy can come off as so nice in the beginning that he appears to be covering up for something bad. A woman might avoid a relationship with him if something just doesn't feel right. What makes a guy too nice or "friend" material instead of dating material? Do you avoid getting into relationships with a guy who's too nice, or is he destined to be a "friend"?