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Dating After Divorce: First Date Baby Steps


Following my earlier articles on life after divorce and separation for men, I’ve received lots of emails. And, they generally have said much the same thing- we like what you say. It’s helpful, but we need practical advice, real world, honest to God, specific tips on what we should be doing. Not a mantra like, Be Positive, Think Happy Thoughts. No, we need something more like Insert Item A in Socket B. After all, we are guys, and need the instruction manual. I’m sure that many of you women reading this are nodding in agreement! If so, don’t read further. After all, this is an article for guys.

OK, ‘nuff said. Let’s talk turkey. For this one, I did some research. I confirmed (or, in some cases, challenged) my own thoughts with a number of eligible, actively-dating females over a wide-range of ages. None of that Cosmo stuff with the Ten Top Things that Girls Look For in a Man, as written by a 20 year old with acne and three dates under her belt, all with guys still living at home. No, just thoughts from people like you and I, that are charter members of the Been There, Done That, Bought The T-Shirt, But Forgot It All Club.

So, what do we need to know? For starters, lots. Remember that we’re now divorced, or separated, and have been out of the dating world for a long, maybe even, long long time. The world, and the women in the world, has changed in that time. And guess what? So have you. Well beyond that new, more ample physique and thinning hair, your perspectives have changed. You view women differently than you did at 21, and your wants and needs are different now. Most importantly, you haven’t thought much about what women want, other than the odd birthday or holiday, in some time. So, making a list of practical tips for dating would take more space than this article. But, we can start with the basics, with more depth to follow in future articles.

Let’s start at the beginning, that first encounter, otherwise known as the infamous First Date. Here’s some of the key Do’s and Don’ts.

DO Take The lead

Contrary to what women generally want you to believe, they like a guy that takes charge. This doesn’t mean ordering for her at a restaurant, or giving her no input at all. Rather, it means you suggesting a place and a time to meet, you making the arrangements. Don’t ask her what she wants to do, where she wants to go, or if she’s sure that she has the time, in between the pedicures. Let her know you want her, and that you’re making the time and necessary arrangements to get to know her.

DO Be Considerate

Don’t suggest meeting at a location that’s all the way across town from her, but happens to be next to your office. Suggest someplace classy, a comfortable, yet casual restaurant or local bar. Not a sports bar. Don’t take her to a movie or a ball game. Not only won’t you be able to talk or otherwise get to know each other, she’s going to label you as one of those Sports Guys With No Time For Me. And, whatever you do, don’t take her to your favorite strip club or to meet your mother, no matter how much you think she’ll like Mom.

A few more items in the being considerate column. Do be on time, although there’s a fair chance that she won’t. Don’t chastise her, yawn, frown, order without her, or otherwise appear annoyed that she’s late. Also, do consider bringing her a gift. I know, it’s wimpy, but do it anyway. If any of your guy friends sees you, he’s going to report you to the local Wimp Society office. But, you will get serious brownie points with her, and with any female within range. And remember, you’re not trying to date your friends. A simple flower is always good. A book or small stuffed animal is also good. Pictures of your ex-girlfriend, Brandi at the strip club, or airline tickets to the Caribbean are not (although the latter opens up an entirely other discussion.)

Do Be Presentable

I know, I know, this is way too basic. But, guess what? The number one complaint of most females at first meetings is that the guy is not neat, clean, or otherwise presentable, indicating that he takes enough pride in himself to be neat in her presence. There have been several studies that summarized, say that the primary things that ladies notice about guys are not 1) muscles, 2) intellect, and 3) car type. I know, it’s hard to believe. Sad, but true. Rather, it’s hands, teeth, and shoes.

So, we need to reinforce this again. Guys, we cannot be too neat. You don’t need to run out and get that manicure, but your fingernails need to be clean and trimmed. Your hair needs to be combed. Your clothes need to be clean and pressed. Wear something that fits the occasion. I know that you love those thread-bare jeans and old comfortable tennis shoes, but consider wearing pressed Dockers and loafers. If it’s a jeans occasion, by all means, wear jeans, but clean, neat ones that actually fit now, not in the 70s when it was first conceived.

DO maintain Eye Contact

Ok, once again, this is the category of kindergarden basics. Maintain eye contact. Period. Women tend to view guys that look away too frequently as either inattentive to them, or shifty, less than truthful. Neither is good for you. Or, they may view you as having a lack of confidence, not take charge. Again, not good for you in any way.

It’s not a difficult thing. When she talks, look at her in the eyes. When you talk, talk directly to her, looking at her eyes. Hopefully, they’re very attractive, so it shouldn’t be a hardship. However, whatever you do, don’t make it a stare-down. Blink, smile, and hold a warm gaze. It’s not a contest.

Do Be Positive

Dating is a stressful experience. There is lots of angst on both sides. What if she doesn’t like me? What if he doesn’t like me? What if he’s a troll? You can make major brownie points by being positive. Smile. Make all positive comments. Or, at least, be neutral. The old axiom applies, “if you can’t say something positive, say nothing at all.” Even if you see her as Hitler-reincarnate, it’s a short term experience. Be positive. They’re all good learning experiences.

Do Avoid The Evil Ex conversation.

Related to being positive, one of the more common complaints of women of divorced men is their need to talk about their ex-wife. Don’t do it. Period. Trust me, it will not help. If you like this lady, save it for a later time. There will be time; she’ll make sure of it as she’ll want to know what went wrong anyway, so that she can understand more about you. Even if you wear a little halo around your head, and your ex was truly evil, you gain nothing by speaking badly of her on a first date. It might make you feel better, but it only raises questions in her eyes.

Don’t Talk About Former Girlfriends

And for gosh sakes, whatever you do, don’t compare her to former girlfriends. OK, it’s not as bad as talking about your ex-wife, but almost as bad. Of course, she knows that you’re not virginal and that you’ve dated. However, she doesn’t want to hear about it. Especially, if she has to hear that she’s the perfect size, just like your former girlfriend, Barbi, except Barbi was more endowed. Sound like something you don’t do? According to dating women, it’s in their Top 5 complaints, aka issues.

Do Be Attentive

Be caring. Open that restaurant door. Carry that umbrella on rainy days. Listen when she speaks. Lean toward her so that she knows that you’re genuinely interested. And, whatever you do, do not do the head turn, or even the eyes away, when that comely waitress goes by. Let her know that you’re happy to be there with her, and hopefully, can’t wait to see her again.

DO Be Communicative, Open

One of women’s greatest issues with men is their perceived lack of communication. Show her from the start, on the very first date, that you can communicate, and that you want to communicate with her. That doesn’t mean telling her your life story, including the ex-wife, and the infinite list of former girlfriends. Or telling her that her makeup really didn’t cover up that zit on her nose as well as she thought it would. Rather, communicating means being comfortable talking to her about where you are in your life. Not just your professional career, but emotionally. It’s ok to tell her that you like dating, or that you want to be re-married, or that you are nervous. Don’t hide feelings or situations. If she suspects that she’s not getting the straight story, the date will be negative for her, even if you do come off as George Clooney otherwise.

DO Avoid Sexual Innuendo or Repartee

The date is going great. You’re having fun, she’s clearly having fun. You’re into her, she seems into you. Do not go sexual. Why not you say? True, she might be into it, have no problem with it. But, more often than not, she’ll come away thinking that you’re moving too fast, worse, that you’re only dating for sex. Contrary to what you might think or hear, women do hate that. No one wants to think that they’re there just for physical reasons. There’s lots of time to get to the sexual side of a relationship. Contain yourself on the first date. You’ll be glad that you did.

DO Take Your Time

Just as you want to avoid, or at the very least, minimize sexual topics on Date One, take your time getting to the physical side of things. True, there are some ladies that will be find it a turn on to sleep with you on the first date. But, most won’t be there after a few follow on ones. Also, are you really sure you want to be with someone that does? Odds are that you aren’t the only fish swimming in that pond. There will plenty of time for the physical side of the relationship. Take your time. Take it a few dates, get to know her, at least to the point that you’re sure being there is what you want. In the long run, you’ll be glad that you did.

DON’T Try to Impress Her

Guys, contrary to what you may have heard, women don’t like to feel like we’re trying to impress them. They want to be impressed by us, as a person, not what we have. Don’t tell her about the five marathons you’ve run if you currently have a beer gut. Don’t bring up the Corvette unless she does, or that you miss your place in Tahiti and really need a travel partner to get there. True, this impresses some women. But those are the ones that are impressed by pretty much anything you, or anyone else, does. Impress her by being open, warm, and communicative with her. Let her discover the Corvette or six pack abs, for herself. She’ll be far more than impressed.

DON’T Be Intimidated

I know, I know, nothing intimidates you. You’re all big, rough and tough men. A little girl in frilly things doesn’t bother you in the least. Then why are there so many men out there that get tongue-tied, or make complete fools of themselves in the presence of a pretty woman? I hear it all the time.

Let’s face it guys; there are those of us who get intimidated. We’re trying to figure out why such an attractive lady is sitting in front of us. She could easily be with any other male on the planet.

Realize that she’s there because she wants to be there. And, she’s not infallible, an angel, or any other apparition. To paraphrase an old sports idiom, realize that she puts on her panties (or thong, as it may be) one leg at a time. She’s human like you are, with all of the same insecurities, wants, needs, and desires. If you happen to have such an angel sitting across from you, don’t wonder why she’s there? Focus on how lucky you are, and make sure that she knows it.

DO Probe Her Background/ Break Up

OK, I know I told you earlier to not talk about your break up. Absolutely true! But, do probe hers. Why? For the same reason that she’s going to want to know about yours, to learn what you’re like in a relationship. If she left her husband because he beat her, that’s one thing. If he left because she drinks, shops, smokes, or substitutes other bad habit, too much, this is more than good information that you need to know.

Be aware here of Murphy’s Third Law of Dating. That is, that the person sitting across from you is an angel. You won’t hear that her marriage broke up because she spent too much time with other men, or drank too much. You’re more likely to hear that her ex-husband took his secretary, Bambi, to Vegas one too many times. Vegas might be accurate, or it might not. All you can do is ask. All information, even modified, is good information.

DO Seal the Deal

If you like this lady, ask her out again. At the table. Before you leave. Why? One, because you’re telling her that you like her, which is very important. Two, it indicates that you’re proactive ,and go after what you want, something that most women find very sexy. Three, it fixes your schedule for Saturday night, and you can always change. OK, I added that one, just to make sure that the women out there who are reading this can have a reaction to this article. Ladies, I didn’t mean it.

Seal the deal. Arrange for a follow up date if you like her. Women hate uncertainly and not knowing where they are in a relationship. Help her out, and she’ll most definitely reciprocate, to your future benefit.

DO Follow Up, Follow Up, Follow up

Guys, there is nothing, repeat, nothing, that ladies complain more about than guys that go away after a date, and are never heard from again. Or, those that are evidently stranded on a desert island for two weeks, with no cellular phone service, and then magically arrive home, call, and want to go out again.

Do yourself a favor, Call her, early and often. If you really like her, send cute notes, email or hard copy. Its fun and she’ll love it. Make her feel wanted. And for gosh sakes, if you somehow, by chance, find yourself intimate with her, send flowers, smoke signals, or otherwise, absolutely positively let her know that you’re thinking about her. Otherwise, if you go to that desert island and try returning, not only will she not talk to you, the word will be out on you, and most of female-dom will also not be talking to you.

Also, help out the rest of us poor guys for future rendezvous, follow up with her, even if you don’t plan to see her again. She’s more likely to still feel positive and warm about the rest of male species. And if the first date happened to continue into the next morning, by all means, flowers!

So, guys, this should get you through that all important first date. For many of you guys, this is all you need, as your social life is a constant series of first dates. But for those of us who the lady is still speaking to the next day, and who actually might like to get to know the female species better, there are those ever treacherous follow up dates. Stay tuned for tips for those in the next installment. Happy hunting!

Dr. Hu Fleming has written extensively about dating and relationships. Stay tuned for his upcoming books in early 2006 on dating for men and dating after divorce.

You can email your dating questions or comments to: drflemingetv@yahoo.com

Dr. Hu Fleming



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