Top 7 Reasons Why Dating Can Be A Challenge

By David Wygant

Dating is meant to be fun.

That is what you told yourself as you were ending the marriage and embarking on being single again.

So how do you deal with the challenges ahead?

Dating is a process a lot of us really can live without. It’s an emotional roller coaster that can drive you to drink four year-old bottles of Mike’s Hard Lemonade from the back of your refrigerator. There are so many ups and downs of dating.

Here is my top 7 list of the most frustrating dating ups and downs and how to feel better about them:

1. We made out in the parking lot and they never called again. Making out is fun! You needed it. They needed it. Don’t beat yourself up that you did it, just realize you did it. You needed some tonsil hockey and to cop a feel. Be okay with it. It was a great date. You were in the moment, and you experienced something that you wanted to do. Plus dating is all about having fun like we did back in College. So make out cop a feel and be like a teenager all over again!

2. I texted them the next morning to say “I had a great time last night,” and they never texted back. So what? You had a great time last night. So did they. They just woke up, and their post-date recap was different from yours. Yes, they probably had a good time but when they thought about it, the chemistry and the “it” factor wasn’t there. It’s not about you. At least you were honest. You lobbed in an honest text. So you did all you can do.

3. Stop the mental post-date recap abuse. You went out with somebody with whom you thought you had a connection, and it turns out you didn’t. So now you’re going to mentally torture yourself for the next four days trying to figure out what you said wrong. You’ll even torture all your friends asking them what you could have done differently to have a different outcome. There is nothing you can do differently after a date is over. It wasn’t the conversation about your drunken uncle that you now think made him think you’re a budding alcoholic. The post-date recap is a form of mental torture. You will never know what that other person is thinking unless they call you. If they don’t call, it really does mean that he or she is just not that into you (which is about the only good advice from that ridiculously stupid book).

4. Should I have said something different in my voice mail message? You left a voicemail message, and now you’re replaying it in your head a thousand times. “Was the way I said ’Last night was fun’ not with enough enthusiasm? Is that what is making the person not call me back?” When it comes down to voice mail messages, the shorter the message the better it is. From an old sales technique, I always prefer to say “Last night was fun. I have something really funny to share with you the next time we speak.” That’s it . . . it creates a little bit of intrigue, a little bit of mystery and no mental torture.

5. Who cares what they think? You left the above voice mail message without knowing if you’ll ever see them again, and they don’t call you back. You start to think “Now they know that I like them ... and they don’t like me.” So what? Is it better just not to do anything? Is it better to just sit there and hope and pray that they call? I always believe in being honest. If you’re the one who left the voice mail message and the other person doesn’t call back, again so what? You’ve got to do what feels right for you.

6. Stop giving your power away to one person. If a two hour date can cause you to give away all your power and confidence, then you need to learn to embrace yourself and love yourself even more. This is just one person you went out with that you knew for two hours. They don’t know what an amazing person you are. The only thing they know is the person they sat across from at the table. Whether they choose to hang with you again isn’t the issue. The issue is that one person does not determine your worthiness. This is just a person that you went out with, and they’re not calling you back. You’ve got toughen your skin. Rejection is what dating is all about. You just can’t take it personally. If I go out with someone and I had a great time, but they never want to see me again, I’m still a great person the next day.

7. In order to feel better about dating, you need to think abundance. Just because you think you like somebody and they don’t call you back, this is not the last person in the world you’re going to meet. In order to be a successful dater, you need to practice abundance. The power of abundance is training your mind that if it doesn’t work out with one person (or ten people), that there are plenty of other people out there that want to meet you and hang out with a fantastic person like yourself.

The next thing you need to do is repeat seven times “There really are plenty of fish in the sea.” You just need to be willing to put your pole out there every single day until you hook the one you’re supposed to be with.

The Dating Aim

By Meredith Goad

Did you know that if you send a quick thank-you e-mail after a first date, the guy is not likely to ask you out again — even though he says he appreciates such gestures?

And ladies, be aware that your date is quietly sizing you up as a potential future mother for his children. But don’t you dare bring up the idea that you might want kids someday, or he’s outta there.

Men often talk about how complicated women are. Well, pot — meet kettle.

These are just a couple of the insights that Rachel Greenwald, a dating coach and matchmaker from Denver, pried from male brains during 1,000 “exit interviews” with guys who never called their dates back.

Greenwald has written two books on dating. The first, “Find a Husband After 35: Using What I Learned in Harvard Business School,” became an international best-seller that was translated into 23 languages. The latest, “Have Him at Hello: Confessions from 1,000 Guys About What Makes Them Fall in Love Or Never Call Back” (Three Rivers Press, $14.99), contains dating advice that’s not always what you want to hear, but is guaranteed to open your eyes.

Greenwald, 46, was born and raised in Denver, but lived in Boston for 12 years, where she attended Wellesley College and Harvard Business School. She spends her summers in Old Orchard Beach, where her grandparents once owned a motel and her mother now has a home.

Greenwald is married and has three children, ages 9, 13 and 15. She and her husband are about to celebrate their 18th anniversary as they do every year — with a nice dinner in a Portland restaurant. While she’s in Maine, she’ll be appearing at One Longfellow Square to give some advice on “My 7 Best Secrets to Find the Right Man.”

Q: Your new book is so detailed and obviously very well researched. But honestly, by the time I was halfway through it, I kind of felt like it’s a miracle that anyone gets into a relationship considering how many immediate assumptions are being made about the other person. Do you feel that way sometimes?

A: I think what has slowly happened in the last few years as online dating has exploded is that there’s this mentality that there’s always a better match just a mouse click away. And so daters’ mentalities have changed. The mentality now is that they feel this almost arrogance that there’s so much volume out there — so many men, so many women — that they’re now looking to rule out instead of rule in. And so I think it’s a miracle that anyone gets together, but this is a recent phenomenon, and it really comes with the arrogance that there’s always someone better out there. You could be out to dinner or to coffee with someone, and you could be back at your home computer in an hour sorting through other singles.

Q: You have all these categories of women that you call “date-breakers,” including The Boss Lady, The Bait & Switcher, The Park Avenue Princess, The Closer. Was there one category where you thought the guys were really being too judgmental?

A: I think both men and women are way too judgmental. I think that we’ve come to create stereotypes so quickly. We just have so much information thrown at us all the time now through social networks and the volume of people that we are exposed to, that our brain has to create stereotypes just to sort through the volume. So I don’t blame anybody.

The category that surprised me the most, I think, was the No. 1, The Boss Lady date-breaker. What was different about it than I expected was I think women go around with the assumption that men are intimidated by their success, and in reality he just doesn’t respond to her abrasive personality. And peeling back that layer, it’s not that she has an abrasive personality, it’s that she is behaving in a social setting the way she has been rewarded at work. She is sticking up for herself, she is overly independent, she’s argumentative, she’s confrontational, and these are all things she has been nurtured and trained to do.

Q: I think it’s a little confusing too, because you always hear guys say that confidence is attractive to them, and they just want women to be themselves. But nearly your entire book is made up of women who were just trying to be themselves and yet men still made all these inaccurate assumptions, labeling them something they were not.

A: Definitely, it’s a tricky line to distinguish what’s confident vs. what’s maybe argumentative, almost. It’s very long interviews with these men. It’s not quick little conversations. So in probing what they really meant by all the things they said, they were very clear in saying they want a woman who is confident and assertive and independent that also has a softer, nurturing side to her, a feminine side. They just didn’t want to feel like their relationship was the same thing as being in the office. Even the toughest Boss Lady has a soft and nurturing side, she just doesn’t show it first. She’s got her game face on.

Q: And your whole point in the book was, whether your advice feels right or not, it’s what you have to do to get to the second date.

A: Right. I definitely don’t want women to change who they are or pretend to be someone they’re not. The point is about sequence. The sequence is the key to the whole thing, to present your soft and vulnerable side first because that is feminine energy and men are initially drawn to feminine energy. But what will keep them is the more masculine energy, almost, that makes you interesting so that you’re not just some arm ornament.

Q: Another thing that could be confusing is some of the guys said that they thought some women were “too nice,” and they considered that to be desperate.

A: Or boring.

Q: I could get off on a whole philosophical discussion about what does it say about our culture that if you are “too nice” or show any kind of real interest in a person, they consider you “desperate”? Maybe they’re just a nice person. I hear that from women too, you know?

A: That’s a really key point that you just made. This isn’t just about what men are saying about women. Women are saying the same things about men. I could have written an entire book called “Have Her at Hello” because clearly this is not just one gender; however, men don’t buy the self-help books they need, so publishers won’t publish them. Women ask me all the time in my lectures, “Why aren’t you speaking to men?” I would if more than seven of them would listen. Everyone on this planet has made false assumptions about someone that later proved untrue. That’s what the focus of the book is about: It is inevitable that first impressions in dating are misleading, so what do you need to do to get past that place so you can really decide if someone’s right for you or not?

You don’t have to like it. No one’s going to read these reasons that men describe and say “Oh, I really enjoyed hearing that,” but it’s what’s necessary to make the connection. And it’s a really hopeful message, because what it’s saying is, “You know that last date you were on when he didn’t call you back? He wasn’t not calling you back because he didn’t like you. He never got to know you. So what do you need to do to allow him to see how really great you are?”

Q: Where did the follow-up e-mail thing come from, and why is that a bad thing?

A: When I was dating, before e-mail, I wouldn’t write someone a letter or I wouldn’t call a guy to thank him, so this whole sending someone a thank-you text or e-mail the next day is also very recent. It was interesting to me to see that it has kind of broken the unspoken male-female code that the man pursues the woman. In the interviews it came up very early on, where a guy would say to me, “We actually had a pretty good date. I liked her and there were maybe some concerns about X or Y, but it was a pretty good date. I’m not really sure why, I just never asked her out again.”

And I would start to probe that. Well, you know, if it was a pretty good date, what happened next, after the date? And inevitably a lot of these guys — about half of them — reported that one of the things that happened next was she sent him a thank-you text or e-mail. And in the same breath that men were saying, “Yeah, that was nice. I appreciate it,” they were also describing something that was hard for them to articulate. They were feeling deflated, like the mystery had been taken out of it or they basically perceived it as a strong signal that she would like to go out again.

And as I started asking about that, many of them admitted they respond differently to a woman they’re not sure is going to say yes or no. They don’t know if she had a good time or not, and part of their DNA, I think, is wired to pursue those who retreat. Not that a woman should be mean or anything like that, but she should preserve a little mystery and play a little hard to get. When you go on a date and you do not like the guy and you don’t want to see him again, do you still send him a thank-you e-mail? Most women don’t. They only send the thank-you when they want to see him again. It really is a signal that they want to be asked out again. It’s a thinly veiled disguise. In poker, you call it a tell.

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