Female Fortnight:
Dating an "Older" Woman

Dating in a woman in her late 30s is nothing like dating a woman in her 20s. Women themselves will admit that how they think about men shifts. That's why I find today's interview so interesting.

Deb is a 38-year-old real estate agent that looks more like a twenty-something, but she's looking for a different type of guy than she was twenty years ago. She freely admits that she's moved on from the "bad boy" stereotype, and the reason will surprise you.

Even if you're not interested in dating women Deb's age, check out what she has to say. That twenty-something will be a thirty-something someday, and it pays to find out just what you're in for.

"Put Yourself Out There"
Interview with Deb - 38, Real Estate Agent, Florida

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

I'm a real estate agent, and I absolutely love what I do. I love getting out there and meeting people and helping them find their dream home. The flexible hours are fantastic, and it's wonderful to know that the sky's the limit in terms of what I want to earn. I can work a lot or a little; it's up to me.

Outside of that, I really enjoy rock climbing, mountain biking, and am even getting started in golfing. A lot of my clients golf, so they've given me lots of pointers.

Are you single and searching?

Definitely! I do a lot of singles events: speed dating, singles clubs, pretty much anything I hear about. You can't meet someone unless you put yourself out there. I'm a firm believer in the power of the mind to attract what you want. You have to put your intention out there in the universe, and you'll attract it.

What do you find attractive in a man?

A keen mind. Someone who keeps up on what's going on in his world is so attractive. You go to parties and there are the same old conversations about who's married who, and who's had a baby, and what's happened on the latest television program. I always gravitate to the conversations where there's real debate going on. And someone who's passionate, who's gesturing, who's really engaging in the ideas, is always the one my eye lights on first.

So someone who stands out?

Definitely. And you know, they're not always the best-looking. I think I speak for a lot of women when I say that what's going on inside is more important. It comes back to the olden days when a man was looking for a fertile woman to bear his child, while a woman was looking for a man to stick beside her. When you meet a man that just radiates conviction, you know that he's going to stick beside his woman, whoever she may be.

So a strong identity is important?

Absolutely. Firm convictions, firm values. I don't care so much if he believes in the same things I do, as long as he stands for something.

And the way a man communicates that is through his opinions?

Not only his opinions, but also in the way he's willing to consider other people's opinions. If you've got a strong sense of self, you're not threatened by difference. You can listen to someone else and see their point of view. It's just people who aren't confident in themselves who have to prove something or prove that they're right.

Does a man's sense of self come through what he wears?

Yes, it does. I just think about the care I take with my appearance. I make sure that I get my hair done professionally, and I always present an attractive image. I keep tanned, I exercise. Sometimes I put on a few extra pounds, and I always make sure I work extra hard to get them off again. I haven't had Botox, but the minute I get those lines in my forehead, I'm going to. I just think that we can't afford to let ourselves go while we're younger, or we'll just get worse when we get older.

How does this relate to what you said earlier about an attractive man not being necessarily the best-looking?

Well, we can do much about what God gave us, but we can do the best with what we have. I want to live a long, long time, and I want to do it with a man who's going to stick with me. I don't want to end up with someone I'm going to have to nurse because he didn't take care of his health when he was young. I plan on rock climbing when I'm 80!

Have your opinions about what is attractive in a man changed from when you were in your twenties?

Most definitely. When I was in my twenties, I was just looking for a bad boy who was going to whisk me away from my family and everything I knew. I wanted adventure. I wanted someone exciting. It just goes to show you how short-sighted I was, because I didn't realize that I could go after that adventure and excitement on my own; I didn't need a man to do it!

Now, I'm much more interested in someone who wants to share my life rather than give me a life. Someone who's interested in being a real partner rather than someone who's going to take care of me. That was the biggest thing I had to learn: that I couldn't wait for a man to come along to tell me what to do.

That's the benefit with waiting until you're older to get married. As a woman, you bring a lot more to the relationship. You probably have a career and are financially independent, and you've figured out who you are and what you really want. A lot of men think that the only thing a woman my age wants is to get married so she can have children before her biological clock runs out, but it's not true. The women I know who are my age and single are that way because they haven't wanted to settle. They've wanted to meet the right person more than they've wanted to get married.

Top 5 Tips to Remember

1. Put yourself out there. Deb has one thing right: unless you put yourself out there, a woman isn't just going to plop into your lap. The advantage with singles clubs and singles events is that, unlike hanging out in a bar or club where you can meet a lot of women who say they have a boyfriend or are just out for the free drinks, the women at singles events are serious about meeting you. They're there because they're available, willing, and ready to give anything a go. Better yet, many singles events, like speed dating, have a high ratio of women to men - so much that men can be dragged off the street to fill up seats! (Compare that to online dating, where men vastly outnumber women.)


2. Think about what you're going to look like in ten years. If you want to still be pulling women at 40, 50, and 60, the only thing holding you back is what you're doing right now. I don't need to give you the lecture. You know what's keeps your body young and what packs on years in a day. Get fit, give up smoking, and give a damn about your health. If Sean Connery can do it, you can, too.


3. Passion is hot. Caring about anything enough to get on fire about it is hot. Doesn't matter what it is; what matters is that you have a passion, and it drives you. By definition, your passion is probably going to be boring to most people, but here's the thing: it's one area in which you are the expert. You know more than anyone else in the room. That's gotta give you confidence.


4. Stand for something. Again, doesn't matter what it is: what matters is that there's something that you believe in and won't back down from. A woman can admire your conviction at the same time she thinks you're wrong. What you don't want to be is the guy who agrees with a woman about everything and has no opinions of his own. It's sexy to disagree. It can even be even sexier to argue. Because there's always making up afterwards.


5. Don't assume all women just want to get married. There's a perception out there that women in their late thirties just want to find a sperm donor before it's too late. Sure, there are a lot of women out there who hit their late thirties and think, "I have to get married now!" But if you reject thirty-somethings on principle, you may be missing out on some pretty confident babes who not only have the experience to be cool girlfriends but are also a lot more experimental and relaxed in other areas that count.

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