Should She Move On?

Terry-

I love your column, and I need advice.

I'm 28, and widowed, with one child. It's been two years, and I've processed everything, and I think I'm in a good place emotionally.

I'm bright, and funny, and a good mom, but I'm not very attractive. Dating is incredibly scary for me.

I have been dating a boy for about three months. He's three years younger than me, and is very nice. He's cute, well educated, etc. We laugh a lot, and share quite a few values.

I think I might love him. He said he definitely has feelings for me, but that he can't call it love yet.

He is scared of falling in love with a single mom, he says, because it's much more commitment than he's planned on so soon. He says he's not ruling it out, he's just not there yet.

After three months, shouldn't he know? Should I chalk this up and move on?

One one hand, it's very likely that he's not ready for a commitment. On the other, he treats me well, and is nice to my kid, and has been extremely honest about where he is emotionally.

I can't tell if he's "into me" or not. He wants to meet my family, he spends time with my child and me, etc. But, at the same time, he's not introduced me to his family yet.

Is this a lost cause? If not, how long do I give it?

-Should I Stay or Should I Go?

Dear Should-

Thanks for writing and for the kind words. One thing sticks out above all else in your letter:

"...I'm not very attractive. Dating is incredibly scary for me."

I'm going to beg to differ here. You're a widow (please accept my very sincere condolences on the loss of your husband), so obviously you are attractive and lovable enough to have compelled a man to marry you. Furthermore, now you've attracted a man (or boy, as you describe him) who says he "definitely has feelings" for you.

You say you're smart and funny. Smart and funny trump looks in the attractiveness department. Have you ever noticed how a person can be magazine-cover perfect, but you don't feel any sort of pull? You're not intrigued. You're not attracted. And then another person comes along carrying a little extra weight around the middle, and maybe his hair goes haywire in damp weather, but he's funny and smart. And he just lights you up on so many different levels.

Same goes for men and you. I once had a beautiful friend who turned heads everywhere she went, but she didn't attract anyone for very long. She didn't have much of a personality.

Dating is scary for a lot of us (I can say this because I am a shy person who masquerades as a not-shy person). Please do not settle for less than you deserve because you fear you're not attractive enough to "do better" on the dating market.

Okay. Back to your boy...

Three months is not such a long time, and it's good that he's been honest with you about his reluctance to fall in love with a single mother. He's right; becoming a stepfather at 25, 26, or 27 years of age is daunting (hell, at age 47 it's daunting).

It's possible he'll get over this reluctance, but it's entirely possible he won't. I don't know that I would banish him, but I definitely would spend less time with him for my own protection as well as my child's (because every minute you spend with this guy, you and the child are becoming more attached to him). He doesn't know if he's going to stick around for the long haul, so you don't know if he's going to stick around for the long haul.

So please act accordingly: He doesn't get to meet your family. If you do decide to go out with him, leave the child with your family or with a good babysitter. At this point, he does not qualify for access to your entire life.

Also, if you aren't already doing it, this would be a good time to spend more time with friends or to make new friends with similar interests. Expand your social circle. If someone else comes along who's attracted to your intelligence and precious ability to make others laugh, by all means, date him. And introduce him to your child only after he's indicated he's not put off by the possibility of one day caring for that little person on a daily basis.

In other words, give your boy a chance to figure out what he wants to do. And, in the meantime, do exactly what you want to do.

And stop holding yourself back due to excuses about being unattractive and afraid of dating.

Terry