From the forums:
I’m in my late 20s and I would guess she’s about the same age as me judging from her looks. How weird would it be to send her an email about this? The news website has her email info listed on it and that is the only contact information that I would have. To me, I think it would be really weird, but I’m tired of not taking chances on girls I’m attracted to (not just looks, but personality, too). I’m kind of picky when it comes to women, but, I’m telling you, this girl seems like one in a million to me. I don’t think there would ever really be any chance that we would meet in person. I also don’t know if she’s single, but she doesn’t wear a ring so I guess there’s a chance.
Anyway, I know this post probably sounds weird and ridiculous, but I just wanted to see if there’s an off chance that anyone thinks this could ever work out. Any advice is appreciated. I appreciate honesty, but if you could please not absolutely tear me to pieces and tell me how terrible a person I am, that would be great! If you say it would be weird, I will totally get it and not email her. Thanks in advance! — Tired of Not Taking Chances
Ok, first, this person you’re talking about is a woman, not a “girl.” She’s a professional who looks to be in her late 20s. She’s a grown woman. Second, no, don’t email her to tell her you think she’s very pretty, seems like an extremely nice person, and you’re interested in meeting her. It will creep her out. Don’t be a creep.
Look, I don’t think you sound like a “terrible person” at all, but I do think you probably have some questionable ideas about women and dating. The fact that you are in your late 20s, you say you are “picky when it comes to women,” that you like meeting new people but it’s difficult for you to meet nice “girls” because you don’t enjoy going to bars and parties (as if those are the only places to meet women), and won’t try online dating, and that you have convinced yourself that some woman on TV is one in a million because she’s pretty and seems nice (it’s her job to seem nice, fyi) are all red flags to me. They suggest that, at best, you are inexperienced and naive and fear rejection to the point that you refuse to pursue anyone whose rejection of you may sting, and, at worst, you are kind of entitled and maybe a little misogynistic.
Why do I say misogynistic? It’s the “picky” line that sticks out to me — that’s usually code for “I don’t like most women,” which… you know, misogynistic. And I say entitled because you want a girlfriend, or at least a date, but have no ambition or desire or interest to do the bare fucking minimum to meet/approach/pursue someone who might be available to you and you are not willing to risk real rejection. That’s entitlement. And it’s not going to work for you. It hasn’t worked for you. It won’t work for you. Emailing some woman on TV you think is pretty and seems nice is definitely not going to work for you.
You know what WILL work for you? Going where there are women available and potentially interested in meeting and dating men. That includes dating apps. (And, hey, if you can email a stranger you think looks pretty and seems nice, you’re a great candidate for online dating!) That includes parties you might get invited to. (Even if you don’t like going to parties, just go, because you know what you probably like even less than parties? Not ever having a date ever.) That includes clubs, activities, and organizations of interest to you (a running club, a political club, a book club, crossfit, freakin’ bird watching, I don’t know). Are you religious? Could you be? Go to church (or temple or whatever). Lots of single people go to church. And some of them are even nice.
Is there time in your life for a part-time job somewhere sort of social – a coffee shop, for example? Taking on a part-time job would expand your circle of acquaintances (some of whom could be potential dates and some who could introduce you to a potential date) and get you lots of face time with the public. (And you know who is part of the public? Single, available women, some of whom might smile at you in the way that a single, available woman who is interested in you might smile. I would not suggest hitting on or asking out a customer, but, at the very least, talking with them gives you a little practice, and should you meet outside of work, you already have a common thread between you and an icebreaker to start a conversation.)
So, in closing: don’t message the news anchorwoman. That does not substitute for genuine effort. Make a genuine effort – step outta your comfort zone, do things that have genuine risk potential, put your ego on the line a little bit, stop being “tired of not taking chances,” and take a fucking chance (but, like, on someone you actually have a chance with, in a way that isn’t creepy, so no fan emails to TV personalities). And stop calling grown women girls.
If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.