Should I let her go this soon?

Hi Meredith,

I have a relationship question and I'd appreciate some insight -- mostly because I'm uncomfortable with the advice that my friends are giving me.

I'm 37 years old and still single. I live alone, am gainfully employed, and either 1) I'm generally disinterested in what I perceive to be the requirements of being in a relationship, or 2) I just haven't found someone I'm truly interested in. Most of friends are married and having kids, and these are the guys I've gone to for advice.

Right now I'm dating a woman who's smart, good looking, and for the most part easy to get along with. It turns out she's also a little insecure, and any issue we've had over the past two months has been about "the attention I give her" (she wants more). We typically see each other once or twice a week, and touch base one other time (text or phone call). Ultimately, to me, it just seems that she's more into this relationship than I am.

Now here's where opinions diverge. I believe I should tell this woman (who's 30 years old and likely pursuing her own relationship goals in life) that this just isn't working out with the understanding that we'd either be seeing more of each other (if I was on her wave-length) or she wouldn't be upset with how often we see each other (if she were on mine). I see this as responsible.

My friends, however, have accused me of being a patronizing idiot who's over-thinking the situation. "Do what you want," they counsel, "and be super clear about where you stand, and she'll do what's best for her." To my question of whether someone with self-esteem issues would ever break-up with someone unless it was unbearable, they simply say "this is why you're still single." I certainly don't want to think or act for two people (another of my friends' charges), but I guess I think in a healthy relationship you shouldn't have to.

And so I'm kicking this one upstairs for further review. Am I over-thinking this relationship? Are my friends counseling me to string her along? What else should I consider (if anything)?

– Damned if I do or don't, NJ

Has it really only been a few months, DIIDOD? If that's the case, you need to give this more time. You're just starting to get to know her.

You also need to stop referring to this woman's self-esteem issues -- because I'm not convinced that she has any. She wants to see you more often. That doesn't mean that she's some wilting flower who feels bad about herself. Please don't frame her loving qualities as personality flaws.

My advice, besides hanging on, is to increase the number of times you see her in a week. Invite her over to watch TV. See if it's fun to have her around more often. I completely understand that you don't want to string her along or make decisions for two people, but you're not doing that just yet. You're figuring this out for yourself because you're clueless. You don't know how you feel about her. If after more time with her you become increasingly ambivalent, sure, by all means, let her go.

The big thing to understand is that this woman isn't a ball of issues just because she wants attention. Humans like attention. You wouldn't want to date a robot. Get to know this human a little bit more and test your limits so that you can make an educated decision about what you really want.

Readers? Should he let this woman go? What do you think of what his friends are telling him? Are there self-esteem issues here? Should he date someone who's more like him? Help.

– Meredith