I met a very cool woman last week. She’s (roughly) 40, 2 kids, divorced a couple of years ago. She’s JUST getting back into dating and has had NO luck at all so far. She isn’t sure how to meet men, and the brief time she spent online resulted in no dates. I asked how long was married. 20 years, she said. She married her high school sweetheart!

So, basically, my new friend is not getting back into the dating game after a divorce – she’s never been in the game! She married her high school boyfriend. She’s never dated multiple guys, met someone at a coffee shop, tried casual sex, flirted with cute men at a party, dated a guy with kids. In terms of dating experience, she’s still a teenager!

And I’ve met many women just like her. And plenty of men too. Over 40, thrust into the life of a single person, with no map, at an age when most people assume they’ll be married or partnered. It can be disorienting, scary, frustrating.

But it doesn’t have to be.

If you find yourself in this demographic – divorced and having little idea how to approach dating – here are a few tips:

1) Know you aren’t alone. Many people, especially Baby Boomers, married young, had kids, and stayed in long marriages until they ended. This is a rapidly growing demographic and there people just like you navigating the same waters.

2) Know it’s okay to be clueless. When you’ve been married that long, especially from a young age, you don’t know anything about dating. And that’s okay. You’re wise in MANY areas, just not dating. But dating is a skill that can be easily learned. And it’s much easier to learn from scratch than to unlearn bad dating habits accrued over years of being single.

3) Embrace the new you. Divorce, while painful and life-changing, is also an opportunity for a new beginning. You’re starting a new stage of your life, a new adventure. This is a chance to reinvent yourself, to do all those things you couldn’t do while married. Take advantage of this opportunity to make your life what you want it to be. When I got divorced, I bought a funky little condo in a part of town I loved, and decorated it exactly how I wanted to, including a GREEN couch I loved. I watched my Sex and the City DVDs over and over and cooked whatever I wanted to. When my friend Jim divorced, he started biking a lot more. It was a sport he loved, and now he could do it whenever he wanted, without having to answer to anyone.

4) Ignore the naysayers. There are plenty of people who will give you a bunch of doomsday crap about how hard it is to meet someone at “this” age, that it’s too hard to meet someone when you have kids, that men only want women half their age, etc. Perhaps even you believe these things. But believing is seeing – if you believe dating sucks, it will. If you have a good attitude, however, you WILL find what you’re looking for.

5) Reach out. There are many resources for the newly divorced to make the transition into your new adventure as smooth as possible. If you’re newly divorced, support groups and meetups are helpful, especially if you’re still working through difficulties. Once you’re ready to date, seek classes, seminars, or a coach. These resources teach everything from where to meet men and women like you, to how to attract the other sex, how to succeed at online dating, tips on dating when you have kids, you name it. I offer these services as well, so stayed tuned for announcements on classes and seminars.

If you’re newly divorced, you’re starting over. Embrace it, get the guidance you need, and enjoy the new adventure.

Never ask someone why they’re single. Why? It puts them on the spot and, more importantly, it pretty clearly insinuates that being single is a bad thing. Being single is NOT a bad thing. There are plenty of dysfunctional people in relationships and marriages, trust me.

If you’re single, I’m sure you’ve had someone ask you this annoying question. How should you handle it?

First, never go on the defensive. You have nothing to defend! The more people see that you feel sheepish about  being single, the more they’ll hassle you. Get comfy in your singleness and recognizes the freedom and independence that come with it. Shrug and say you enjoy being single. Or say confidently that you’re dating and hoping to meet the right person. When I was single, I rarely got this question. I feel pretty strongly it was because I truly enjoyed and embraced being single. Did I want to find someone? Sure! But I was comfortable in my own skin and never felt like being single was liability, and people picked up on that fact.

If you get this question a lot, especially from people you don’t know or don’t really like all that much, try responding with humor. The suggestions below come from Julia McCurley, an Austin-based matchmaker who works with single people full time. Numbers 9 and 15 are my LOL favorites!

1. What? And spoil my great sex life?
2. Why aren’t YOU dating/divorced yet?
3. It gives my mother/father something to live for.
4. I’m not willing to give up on love just yet.
5. Just lucky, I guess.
6. I already have enough laundry to do, thank you.
7. Is this a proposal?
8. Because I think it would take all the spontaneity out of dating.
9. I’m waiting for you to get divorced so I can marry your wife/husband.
10. It didn’t seem worth a blood test.
11. The mail order bride/groom hasn’t arrived from Russia yet.
12. I’m not done “boozing and whoring.”
13. Because having both a husband and a child would be redundant.
14. I’d have to forfeit my billion dollar trust fund.
15. I’m waiting for your son/daughter to turn 18.

Join in the conversation! How do YOU handle this annoying question?

A few weeks ago, I wrote a post outlining several reasons a man or woman may not have married by the time he/she reaches 40. You can check it out here. A reader and regular commenter asked a good question, which was:

“Why is it that once someone reaches their late 30′s (especially male), the status of “never married” is considered to be more of a red flag in dating, than “divorced”?”

There is some truth to this. But why?

As I discussed in the first post, being never-married at age 40 puts you outside the “norm” – i.e. not on the hump of the bell curve. And anytime you fall outside the norm, people wonder about you (or at least notice you). We all notice the guy with the tattoos on his face at the gym. We all notice the woman who’s 6’2″. We wonder about those people who have polyamorous relationships. Why? They’re different than most people. It’s human nature to notice what’s different. And, unfortunately, “noticing” can turn into “judging.”

Yes, a woman may consider a never-married man pushing (or over) 40 a Red Flag. Why? Statistically, it’s far less common than a man of the same age who’s divorced. She will wonder. However, if you’re 25, being never-married is the norm, and being divorced is far more unusual. In this case, being divorced becomes the Red Flag.

However, to rule out a guy only because he hasn’t been married by the time he’s 40 isn’t really fair. As I discussed in Part 1, there are many reasons a man may be in this position, especially in this day and age. Many of those reasons are not problematic for most women. The problem is, many women fear that the reason IS problematic – i.e. that he’s got “issues” or is commitmentphobic. And for a woman who wants marriage, a commitmentphobe is the worst type of guy to date. So she’ll opt for a divorced guy, who’s demonstrated that he’s the marrying kind.

As a never-married guy nearing or over 40, if you want to meet the right women for you, it’s important to know what you want. As I discuss in Changing Your Game, knowing why you’re dating is one of the most important factors in getting what you want from women. And many men aren’t clear on what they want. If you know you want marriage, it won’t be hard to convey that to women, which will increase your options with marriage-minded women. If you aren’t ready for marriage, but want a committed relationship, you can convey that as well, avoiding marriage-minded women and attracting women who want what you do. Whatever you want, there is a woman out there who fits your needs.

Fortunately, people are marrying later and later, and choosing to delay (or skip) marriage is becoming far more common. Rather than making snap judgments about a never-married man close to 40, get to know him a little. And remember, more than 90% of people marry eventually. It just takes some longer than others.

And here’s a tip: it’s OKAY to be outside the norm! Sure, people may wonder about you, but they may also find you interesting, innovative, or admirable. This is especially true if they sense you are comfortable with who you are.

If you haven’t heard already, the story about the guy whose Match.com spreadsheet went viral has all the social media and dating bloggers commenting away. You can read the story here – but the nutshell version is 20-something guy maintains a spreadsheet of the women he’s interested in on Match.com. He meets a woman and decides to share it with her; she distributes it; it goes viral. Media maelstrom ensues.

Many have criticized spreadsheet guy for rating his potential women (7.0 vs. 9.5), for his comments (“very jappy”), for even creating a spreadsheet at all. He’s been called “creepy,” “ridiculously nitpicky,” and a “cad” for treating women like “statistics” and for courting so many women at the same time.

Seriously?

What exactly did Spreadsheet Guy do that warrants this kind of judgment? More importantly, what did he do that most single people don’t already do?? Hell, even the worst of his comments (“very jappy” – which, by the way, refers to JAP or Jewish American Princess) wasn’t all that bad. I’ve heard FAR worse from other single men, AND FROM SINGLE WOMEN. Far worse. All he did was use a tool to help him keep track of his dates.

And the juggling multiple women. So? Since when is it a crime to have options? When you date online, often you will chat with many people at once, go on a “meet and greet” with a few of those, and then, if you’re very lucky, find someone worth seeing for a while. Welcome to dating online.

Spreadsheet Guy simply put in Excel what most people do in their minds. We meet and date people, and we evaluate them by how attractive and interested they are to us. When dating online, you have a lot of people to evaluate at once, so comparisons are natural. Yeah, it’s weird to see someone’s personal logs about you, just like it would be horrifying to be able to read others’ private thoughts. But we aren’t supposed to see them.

The problem here isn’t the spreadsheet. I keep spreadsheets. Many, many spreadsheets. I kept one while I was on Match. Why? For the same reason he did – to keep track of people. And to learn something. And because I’m a spreadsheet sort of person.

Spreadsheet Guy’s ONLY mistake was sharing his Little Black Book. Some girl got offended, and then made the even bigger mistake of forwarding the information on to multiple people. This is where the entire thing went awry. But he’s owned up to his mistake and handled the situation pretty well.

What do you think of this situation? Speak your mind here!

So I got a message on Facebook from a friend in the film business – Roger Ebert had just reviewed the movie Think Like a Man. The movie, which comes out in theaters today, is based on Steve Harvey’s dating book. Apparently, “based on” is putting it lightly, as the book is prominently placed and discussed throughout the entire movie.

You probably don’t want my opinion on comedians giving dating advice. In the end, if the advice works for you (and you like waiting at least 90 days to have sex with someone you’re dating), then it works for you. This isn’t about Steve Harvey or his book. It’s about what Ebert said about dating books. You can read Roger Ebert’s review here, but here’s the good quote:

“Anyone who reads advice books about romance has one problem to begin with: bad taste in literature. The idea that a book can advise a woman how to capture a man is touchingly naive. Books advising men how to capture a woman are far less common, perhaps because few men are willing to admit to such a difficulty. “

Ebert also made somewhat similar comments in his review of the movie He’s Just Not That Into You, also based on a dating book of the same name (also written by a comedian). To him, the advice for women was startlingly obvious.You can see my comments on this here.

Not everyone likes the idea of reading a book with dating advice in it. These are often the same kind of people who ridicule the idea of reading any self-help book and can’t bear the thought of going to therapy, including marital therapy. They say things like:

• “You can’t learn dating from a book.”  (just heard this comment the other day from a single man in his 50s)
• “You should be able to fix your own problems.” (heard this one from someone who never figured out his problems)
• “I don’t trust people who try to make money off helping other with their problems.” (yet another quote from someone commenting on – yes – a dating advice blog)

These same people have no problem reading books on finance, business, parenting, or home improvement. Well, guess what? Those are all “how to” books. They are ADVICE books. Why is it natural to seek legal, financial, or medical advice, but somehow we’re supposed to automatically know exactly how how to date, have relationships, and understand the other sex? This is the way many people used to think about online dating – oh the horror of having to pay to find a date online!! Now everyone’s doing it.

Guess what, Roger Ebert? You’re wrong. You CAN advise a woman on how to capture a man, and you CAN advise a man on how to succeed with women. How do I know? I’ve done it. So have my colleagues, through books and through other even more unusual methods – coaching and matchmaking. And I’ve gotten a LOT of feedback saying how much my advice helped them. Rog, believe it or not, not every woman knows that if a guy gushes about how much he enjoyed your date but doesn’t call for a week, he isn’t that interested. Not every guy knows that mentioning your divorce or ex on a first date is a big no-no. Not every online dater knows that making negative remarks in your profile makes you look bad.

See, Rog, you’re a Boomer. You were raised in an era where there were no dating books. You had to figure it out on your own. Most people from your generation fall in love and marry young. If they get divorced 10 or 20 years later, they are often lost when it comes to dating. And you’ve been married for, what, 20 years? My guess is, you don’t know much about dating or have forgotten what it’s like.

“For both sexes, I recommend a good novel, offering scenarios you might learn from, if only because they reflect a lot of doubt.”

You really want people to learn about dating from reading fiction? Sorry, man, but that sounds far crazier than reading dating advice books!

I still like your movie reviews, Roger Ebert. They will always be the ones I read first after watching a stellar film. But don’t knock a genre of books you know nothing about. Email me – I’ll send you a copy of Changing Your Game, my book for men, and you can see what dating advice is really about. I’ll make a believer out of you yet!

Every generation has an age where, consciously or otherwise, we expect to be married by. In the old days, it was 30. In more modern times, it was pushed back to 35. Now, it’s 40, and likely still increasing. These expectations are based on what society is doing – the earlier the average person marries, the earlier we’re expected to marry. These days, the mean age at first marriage is at an all-time high: 26 for women, 28 for men.

Whenever you discuss “means” or “averages,” that’s a number to represent a much broader distribution. However, this distribution is (somewhat) bell-shaped, in that the bulk of the population doesn’t deviate too far from the average. So what happens if you do? I’ll tell you what happens: people will wonder. Why? Because people wonder about anyone who deviates from the norm. They can’t help it.

So, as a single person, what happens when you meet someone who is past a certain age and hasn’t yet been married? Do you assume there “must be a reason?” Do you assume the worst, that the person is unmarryable, that if he or she were a good partner they’d be married by now? Many people think such things. But they aren’t often fair.

Yes: if someone is over 40 and never been married, they are outside the norm. Yes, there probably is a reason for the deviation from the norm. But does that reason have to be a negative thing? No. Does that reason make that person a poor partner? Not necessarily.

There are many reasons a person may delay marrying. Here are several you may not have considered:

Career. Some people choose to focus heavily on their careers in their youth. Let’s face it: trying to manage a career and a relationship/family in modern times isn’t always easy. Most of us don’t live near our parents, who can help take care of children, so sometimes it’s easier to just put off marriage/family.

Late Bloomer. Some people take longer to develop the desire for marriage, or the maturity necessary to take that step. Marriage is a big step, and sometimes it’s easier to postpone it until you’ve done all the “single” things you want to do.

Shy/Socially Awkward. Some people want marriage at a younger age, but simply lack the social skills necessary to meet the right person. So it takes longer for such folks to meet their other half. When they do, they’re often excellent partners.

Personal Convictions. Some people value long term commitment, but don’t want or need the legal part of marriage.

Commitmentphobia. There are plenty of people who want marriage or its equivalent, but have deep-seated fears about actually doing it. They get involved in relationships, then drag their feet when it comes to pulling the trigger, terrified they’re going to lose their freedom or marry the wrong person. When people fear getting involved with never-married people over 40, it’s often because they fear the commitmentphobe.

These are just a few examples of why a person may not be married by age 40. As you can see, many of them are not problematic. When you meet an unmarried single over 40, don’t assume the worst. Get to know them. Yes, there’s a reason they aren’t married yet. But the trick is to figure out if that reason is a problem for you, or not.

When you browse online and search for people who interest you, at some point you’re going to have to send an email. And most of the time, it’s the guy who sends the email. I’ve always said that women should email men online and initiate things, and some women do, but that’s another blog for another time. As I discuss in Changing Your Game, the first email you send to a woman is important and says a lot about you, so it’s important to avoid saying anything that will scare her away.

Here are a couple of examples:

Sex. Never, ever make any kind of sexual remark, suggestion, innuendo, or any reference whatsoever when you email a woman online. This includes mentioning how hot she looks, how great her body is, how sexy she is. Coming from a man you’re comfortable with and interested in, these are great comments; coming from a stranger, they’re creepy. And most men know to avoid anything more sexual in nature – what you want to do to her, what you want her to do to you, sending pics of your junk – women hate this, even the ones who may be interested in NSA (No Strings Attached). This advice may sound obvious to you, but a colleague of mine said she gets TONS of email online and gets a bunch of emails of a sexual nature. No, no, no.

Complimenting her beauty. Less obvious (but still problematic) is complimenting a woman’s looks. This week I talked with a client who remarked that men would email her and tell her how beautiful she was. There is NOTHING wrong with telling a woman she’s attractive and women do enjoy hearing this – but not right off the bat. Why? Because it sounds like you’re only interested in her looks, which comes off unsophisticated and untrustworthy. If you’re emailing her, it’s because you find her attractive. That’s a given. So in the email, focus on other topics instead.

So What DO I Say?

Usually, a woman’s profile will have something you can use to email her. She’ll mention her job, her love of skiing or the Dallas Cowboys, that she has two dogs, her recent trip to Cambodia, or something like that. Ideally, something in her profile (other than her photo) interested you. If not, your odds aren’t good. If so, dial in on that in the email. By doing this, you greatly increase your chances of getting a reply. Why? Because you showed interest in HER, in something that matters to her.

Also, find common ground. Do you work in the same field? Enjoy the same hobby? Both love the Yankees? Share a love for golden labs or Thai food? Mention that, no matter how insignificant. Common ground helps break the awkward ice that is online dating.

Remember: the trick to online dating, at least early on, is getting someone to feel comfortable with you. If a man can do this, he will have more options with women.

The first date is important. It establishes whether there is chemistry between the two of you, how well you interact, and whether there will be a second date. Psychologically, the first date represents the beginning of a relationship, whether that relationship lasts one evening or twenty years.

Comfort is Key

As I discuss in Changing Your Game, people are nervous on first dates. It’s human nature to feel uncomfortable when you’re out with someone you hardly know and you know that, on some level, you’re being evaluated. It’s much like a job interview, only more personal. Thus, because most people are nervous on a first date, picking a good first date venue is important. In general, you want to pick a place/activity that makes you and your date feel more comfortable, and avoid places that increase discomfort. Times this by 10 if you met on an online dating site.

Good Places for a First Date

Ideally, choose a restaurant, coffee house, or bar (if meeting for a drink) that’s familiar to both parties, or a new place that’s popular and well-liked in your city. Make sure it’s quiet enough to chat, not too crowded, and has good ambiance. Avoid dumpy or loud places. If you feel unsure of the place you chose, run it by your date and gauge her reaction. The more positive the reaction, the better.

Find out what your date likes or wants to try. If she loves Indian food, give that a try if you also like it. If he’s a beer-drinker, choose a popular pub to meet for a drink.

Stay in public places. Guys, if you take a woman somewhere private or isolated from people, she won’t feel comfortable. Save that for later dates.

Also, keep the place appropriate to your level of acquaintance. Online first dates should start with coffee or a drink, or (at most) a brief lunch during work. Lunch is for someone you feel more comfortable with (perhaps because you’ve already met before in person), and dinner is for someone you feel romantic about (because you already know that person from work, your social circle, etc).

The more you attempt to make your date feel comfortable, the more likely you are to get a second date.

Date Venues to Avoid

Here are a few date venues that increase discomfort, and why:

• Bars and clubs. Too loud, crowded, and difficult to chat. If you’re meeting for a drink, pick a restaurant bar or a quiet pub. Patio bars are great in summer.
• Parties. On top of trying to connect and make a good impression with you, now your date has to worry about doing the same with a bunch of other people too. Far too nerve-wracking for a first date.
• Weddings or family events. Much like a party, but worse because it involves family, not to mention the topic of commitment. Again, too much pressure.
• Long or involved dates. Avoid any date that will last more than an hour or two, which will already seem like a lifetime if things don’t go well.
• Activity dates. A first date is too soon for a run, bike ride, hike, etc. What if one of you is out of shape or far slower than the other? Do you really feel comfortable wearing spandex or shorts with someone you hardly know?
• Your place. Women should avoid this for safety reasons. Even if it’s someone you know, it’s hard to feel comfortable in someone else’s home. Stick to neutral territory.

Of course, every one of the above places can be good, even awesome, for later dates.

You may wonder, doesn’t something novel, challenging, or exciting actually make a date better? Yes. Studies have shown that emotionally stimulating activities (physical activities, scary movies, etc) can bond people together. But what’s exciting for a 3rd or 4th date is too much for a first date.

What is the worst first date place you’ve ever had, and why?

A new article came out in The Daily Beast, entitled “Why Men are Settling for Mrs. Good Enough.” The article includes an interview with Helen Fisher and some very interesting quotes and stats based on a recent study that included 6,000 people. Jessica Bennet, who wrote the article, says:

Rather than living up to the stereotype of commitment-phobic bachelors, modern men reported that they fell in love just as often as women, were just as likely to believe that marriage is “forever,” and scarcely bit when asked whether they’d prefer to “just date a lot of people.” But most shocking was how many of the single men wanted to settle down—and how willing they were to lower their standards to make that happen. A whopping 31 percent of adult men said they’d commit to a person they were not in love with—as long as as she had all the other attributes they were looking for in a mate…

To illustrate, one married man in his 40s was quoted as saying: “My wife isn’t perfect. She isn’t the best I’ve had in bed. But she’s a wonderful mother to our daughter, she’s very helpful in our business life, and we get along very well.”

Many people still subscribe to the belief that men don’t want marriage or family, or that they insist on chasing the Hot Chick. However, this research suggests that men take marriage seriously and are willing to think hard about the sort of traits they want in a wife.

What’s interesting in this article is the idea of “settling,” or stepping away from what you really want in order to get married and start a family.

I could go on and on about this, but I’d rather open this up to discussion. Check out the article. What do you think? Whether you’re male or female, does this article fit with your experiences? Is it “settling” to marry someone who isn’t your ideal, or just realistic? Do you think men would really marry someone they aren’t in love with?