Female Fortnight:
Dating Powerful Women

The most desirable women aren't always the 10s. Sometimes, they're the women with the powerful jobs: you know, power suits and briefcases and a flasher car than yours.

Dating one of these women can pose some unique challenges, not the least of which is figuring out where you fit in with relation to her career.

That's why this interview with Hailey is so interesting. She gives us some tips about what it's like to not only be a powerful woman but also what it would take for her to consider a one-night stand, what creates chemistry, and what the best thing a boyfriend ever did for her was.

"See Me As a Woman"
Interview with Hailey - 29, Deputy District Attorney

Describe yourself: what you do for a living, what you enjoy, etc.

Well, I'm a deputy district attorney, which sounds really amazing, but trust me, the job is not. There are some aspects of it I really like, like going out on drug busts, but, you know, it's just work. I never thought I'd be doing this. I was always the creative person at school. I was really good at art and drama but hated anything like debate. I'm not really sure how I ended up in law school!

Are you single?

Yes, I'm single, still looking! Haven't found anyone yet.

What do you look for in men?

What do I look for? Let's see ... good-looking, of course. Dresses well. Has nice shoes. Smart. Gets along well with my parents. I have a big family, so family is pretty important!

Anything else?

I mean, if the right man came along, that would be great, but it's not like I'm looking. I work in this totally male environment where I need to be taken seriously. I laugh with the guys, I joke with them, sometimes I go out drinking with them, but, it's like, I'm not a guy. Sometimes they'll hit on me when they're really drunk, but, you know, just for sex. I guess, if I really thought about it, what I want is someone who sees me as a woman rather than a district attorney.

Can you explain that further?

If I were to have my ideal relationship, it wouldn't be anything like work. It would be someone who knew me as I was with my family, totally outside the context of my job. Actually, ideally it would be someone who didn't even care what I did for a living. All they cared about was getting to know me, my thoughts and opinions. How many guys ask you that? Rather than asking you what you do, how many guys ask you what you think about something or what you care about? Sometimes I don't even like telling guys what I do, because I feel like they change afterwards or stop wanting to talk to me, like they're afraid of me or something.

How could a guy make it clear that he was seeing you as a woman rather than a district attorney?

Ask me about my family, I guess. Ask me to dance. Flirt. Flatter me. Maybe it's the confidence that's so attractive, when a guy isn't expecting me to take the lead or waiting for my reaction. I hate that. It's like, a guy comes up to you, and then he acts like you have to give him permission to stay there and talk. A guy should be confident enough to join in the conversation I'm already having with my friend or join our group, you know?

Where do you meet men?

The last guy I met through work. I try not to date anyone that I have to work with regularly, you know, keep work and dating separate. But still, work is the easiest place to meet someone. Or if not work, then when you go out with your co-workers. A friend of mine met her husband by joining a soccer club, which I thought was really neat. Another friend met her husband when she was waitressing. A lot of my friends hooked up in college.

Do you think a guy could approach you anywhere?

Anywhere? Like on the street? Probably not. I'm usually pretty cautious around strangers. You know, I work with some pretty nasty sorts, so I've seen the kind of psychos out there.

What could a man do to make you trust him?

That's a good question. Probably not want anything from me. That's the biggest one. With some guys, you can tell that they want things to go a certain way. Like, they want to ask you out, and the entire conversation is just a lead-up to that question. Or they want to have sex with you, and they're just putting in their time until you get drunk enough to say yes.

Isn't it okay for them to want sex with you?

Sure! Of course! I mean, they can want it, but that doesn't mean they'll get it.

What do they have to do to get it?

Am I supposed to really answer that? I guess they have to be good-looking and all the things I said before. I suppose I'd consider a one-night stand if the guy was really attractive and there wasn't any chance of having more but that one night, like, if a guy was traveling through or something, but I tend to prefer to get to know someone first. Find out a little bit about them. Know if they're a good person or not.

So you'll sleep with anyone if they're good-looking and a good person?

No! I mean, obviously there has to be chemistry.

So what creates chemistry?

If I knew that, I wouldn't still be single! I don't know. There are a lot of nice guys I wish I was attracted to. I think part of it, for me, is respect. I have to look up to someone before I'll want to sleep with them. There's no point in me being with someone I don't respect. It's like, I want to feel like I'm reaching up to be with that person, like they're challenging me to operate on a higher level. I don't feel that way with most guys. With most guys, I feel like I do with the guys at work: they're nice and nice-looking but they're more like brothers. To be a lover is something different. It's like, to be a lover means to bring out the woman in me. It's a different mindspace. I really feel like the person has to see me as a woman and appreciate just that ... femaleness about me. Not be impressed by me.

What was the best thing a boyfriend ever did for you?

When my ex and I used to live together, he'd always do little things like do a load of my laundry or set a pot of coffee on right before I was about to come home... The other amazing thing was that he'd actually remember little things I said. Like, I'd mention that there was a movie I was wanting to see, and I'd come home one evening and he'd have rented it. You know, almost like reading my mind. It felt so good to know that he was there caring for me and watching out for me. Work can get really stressful, and just knowing that I wasn't going to have to come home and keep everything going on that end really helped.

Do you have any tips for guys who want to get better with women?

Probably just to see through the clothes and the job and just see her as a woman.

Top 5 Tips to Remember

1. Relate to a woman as a woman, not as a professional. In an earlier interview, model Sarah said the same thing. She was tired of her boyfriend seeing her as a model rather than as the person that Sarah saw herself as, which was a budding interior designer. Especially for powerful women, their job can be a huge stumbling block when it comes to meeting men. Not only do they have to be careful with how they behave in public, in case their behavior gets splashed across the papers, but they also have to be more cautious about who they trust. Get around this by relating to a woman on an emotional level rather than playing 20 questions about her job. If she wants you to know what she does for a living, she'll volunteer the information.


2. Be aware of your expectations. Hailey's not the only one who can sense when someone has expectations about how things will turn out. Expectations, whether they're conscious or subconscious, can completely kill an encounter. Don't expect anything, and learn to enjoy what happens regardless of whether it's what you expected.


3. Get interested in what's important to this particular woman. When you start a conversation, you're probably going to be covering a wide range of topics until you hit on one that makes her eyes light up. For Hailey, it's talking about her family. When a woman talks about something she's passionate about, she gets stirred up emotionally, and she will attribute her emotional arousal not to the subject but to the person who got her started on it - you.


4. Avoid treating a woman you're interested in like one of your buddies. We all know women that are great fun to pal around with. You get the sense that Cameron Diaz and Drew Barrymore would be perfectly happy being one of the guys. But if you treat a woman like one of your buddies, you change the dynamic of your interactions from potentially sexual to purely platonic. Show that you respect a woman's femininity by doing the little things, like pulling a chair out for her. You don't have to treat her like a glass slipper, but showing her that you see her as a woman rather than a pal will set the stage for something more.


5. Keep your eyes open at work. Career women spend a lot of time on their jobs, and they're not as likely to be out hitting the clubs on the weekends. So keep your eyes open at work. Where I live, there's a particular coffee shop that all the professionals hit at 10:30 a.m., and there's no better opportunity to start up a conversation than when you're standing around waiting for coffee. Dress to fit in. If you normally wear khaki shorts and t-shirts to work, try upgrading your wardrobe. A professional woman will feel more comfortable with someone who's dressed as her equal.

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