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Dating After 35 - Expert Advice


Best-selling author and dating coach Rachel Greenwald answers your questions about dating, romance and finding love a bit later in life.

o doubt about it: Dating becomes a different game as you move through your thirties and onward. How do you talk about your past? How do you talk about your hopes for the future? How do you avoid coming across as desperate? We have the answers: Happen recently had a chat with Rachel Greenwald, dating coach and best-selling author of Find a Husband After 35 (Using What I Learned at Harvard Business School). She answered questions from real people like you—about finding love at any and every age. Listen to her wise advice.

Q: What is the most important change in the dating world in the past 15 or 20 years?
Rachel: Undeniably, the most important changes have been technological—specifically online dating, and also e-mail exchanges—where friends introduce friends and network through e-mail. So for those of you who are a little rusty on the computer, you will definitely want to get a tech-savvy friend or relative to get you up to speed. And, understand that even if you don't like it, or feel uncomfortable with it, the Internet is here to stay, and is absolutely a part of the fabric of dating today.

“The most important change in dating in the past 15 years is undeniably the electronic aspects, such as e-mail and online dating.”
Q: I have a feeling that I come across as too needy, when I'm just trying to be friendly and inclusive. Am I better off playing hard to get?
Rachel: Men and women can smell desperation a mile away, and if you have received feedback that you appear too needy or if you sense it in yourself, then you absolutely need to tone it down. Ask friends or dates (if you have communication with them later), what specifically you did that appeared needy. It may be something easy to change, such as too much talking about being lonely and needing a father for your children. But whatever your behavior or communication that projects a needy image may be, it needs to stop, because it's a huge turn-off.

Q: Is there really a difference between dating at age 28 and dating at age 38, or is it all just a state of mind?
Rachel: I think that dating at age 28 can be more leisurely; you have a bit longer to get to know somebody before deciding the relationship is or is not right. If you're a woman who wants to have children, you're still in a place where time is your friend. By age 38, however, you need to be more efficient in dating, both by increasing your efforts to meet more people, and decreasing the time you're willing to spend with someone before deciding if this is The One.

Q: I'm at a loss. Other than the bars, where can I meet men in their 40s?
Rachel: This is a great question! The reason it's great is because it's the wrong question—everyone assumes that it is difficult to meet men because they don't know where to look, but after 35 there is no where, there is only how. You have to use several different strategies. For example: Online dating, asking friends and relatives to fix you up, speed dating, matchmaking, going to join new clubs and groups that interest you.

“Here’s my proven Date/Sex Rule: You must go on a minimum of 16 dates (over 2 months) before having sex.”
Q: What does a single 37-year-old woman who still wants a child do? Are women like me in a hopeless situation?
Rachel: Women like you are absolutely not in a hopeless situation—you’re in a very common situation. I suggest you see your 37th birthday as a wake-up call to mistakes you may have made in the past, such as working too many hours and sacrificing your dating life or spending too long with the wrong man. Consider it jumper cables to jump-start your dating life.

Q: I am told I am intimidating, that I give off the aura that I don't need a man. How can I change this?
Rachel: I hear this question a lot—it is a very important issue for successful women today. First of all, what you've described as intimidating may come across as arrogant or overbearing. I want to challenge you to ask six friends and co-workers tomorrow to describe how you come across to someone you've just met. (And don't use the leading question, “Do I come across as intimidating?”) If you do hear that you’re intimidating, realize that you’ve been given some very valuable information about your communication skills. You need to soften your approach early on, to give someone a chance to get to know you better. So, for example, instead of telling someone you're the president of a real estate company, try telling him you work in real estate. In a first date situation, simply restating your profession might relax him, and get him to see you in a different light.

Q: I really built my whole world around my marriage and my ex. I'm so lonely now, but just can't make the leap to dating again. What do you recommend?
Rachel: First of all, you have to decide when the time is right for you to date again. Only after you have truly mourned the loss of your ex, can you make dating your number one priority. Then, get busy! You need to clear the path in your schedule—whether that means getting extra babysitters, slowing down at work and not taking on extra projects, or delaying that home renovation. Everything you do and every person you meet has got to be seen through dating lenses, because doing anything half-hearted is not going to get you the result you want. Just as you would when searching for a job, you have to make dating your first priority.

Q: What are the chances of marriage at the young age of 63, and how do I find it?
Rachel: Your chances are as strong as the effort you put into meeting someone. If you put 100 percent effort in, then I believe firmly that your chances are 100 percent. However, most people only put in 20 percent effort. I understand that everyone has busy lives and other commitments, but try to make finding a mate a top priority for a time, and try to focus your attention on every dating activity you can think of (in my book there are 15 steps covering all dating activities) that can bring love into your life quickly and efficiently.
Single parents need to beef up their babysitting lineup and not feel guilty about it.


Q: I'm a 37-year-old single professional mom, and I don't go out. How do I find a date that is right for me?
Rachel: Working mothers may have a much more challenging time, but it is by no means impossible to re-work your calendar and your commitments to carve out more time to spend online dating and socializing. The key is to beef up your babysitting lineup, and not feel guilty about it. Even though in the short term you may not be there in time to tuck your child in to bed on a particular night, in the long run you are helping the child by bringing in a father to help guide him and love him. There are many single-parenting social groups that you should join and you can find a list of some of them in the appendix of my book.

Q: How can we compete with females half of our age, the ones men our age are attracted to?
Rachel: That is a very real dynamic in the dating world, and I'm not going to pretend that it's not a challenge. I would encourage you to keep an open mind, and ask yourself, “If men my age think I'm too old, which age group thinks I'm young?” And the answer may be men 10 or 15 years older than you. Please don't rule them out for their age alone, because what you're looking for is happiness, not birthday candles.

Q: Where did you get the inspiration for this book?
Rachel: I was inspired by my first client, over 10 years ago, who was also a good friend of mine: a 40-year-old single woman who was smart and attractive and fabulous, and who couldn't find a mate. While my infant took his naps every afternoon, I sat on the phone with her and talked to her like I used to talk with clients when I worked as a marketing director. I told her about marketing and packaging and branding, and translated those concepts into the dating world. Within 10 months, she had used my advice to meet the love of her life. Sitting in the audience at her wedding, I realized I needed to write a book.

Q: I've met two men through my kayaking hobby, but neither turned out to be what I'm looking for. Are similar hobbies really a good basis for meeting someone?
Rachel: Well, you've learned that the answer is no, so go in the opposite direction and join groups where you have absolutely no experience. For example, sign up at your local adult education center for a class in furniture making, or Web site building, and see if there's any difference in meeting people who have skills and interests that are different from yours. My guess is that you will find a lot of interesting people outside the hobbies you already know. If one thing doesn't work (such as your kayaking group), then try something completely different. Shake it up!

Q: Is it really bad for a woman to have sexual relations with a man when they've only gone out with a couple of times?
Rachel: Absolutely! This is my big pet peeve. Here’s my proven Date/Sex Rule: you have to have a minimum of 2 dates per week, regularly, for 2 months (minimum 16 dates total) before having sex with a man. You must pace your relationship, and let it build steadily. If you rush into intense physical relationships too soon, they usually crash and burn. This rule may seem excruciatingly old-fashioned, but it ensures that your relationship is reasonably stable, because you have seen each other regularly over a substantial period of time. Also it encourages him to look at you as a possible wife, and not a one-night stand. If he's looking for casual sex, this Date/Sex Rule will screen him out, and that's good news for you.

Q: Do men think differently of woman who has never been married at 35?
Rachel: Not at 35, but probably at 45, if you want the truth. I think 20 years ago men might have thought differently about women who were never married at 35, but today 35 is truly the new 25. But I'm a marketer and can put a good spin on anything. If you're are 35 or older, you can explain your status by the amount of time you devoted to your job or education, and all of the exciting things you've done in your life during the past 10 or 15 years when most of your friends have been getting married.


Rachel Greenwald is the author of the New York Times best-selling book Find a Husband After 35 Using What I Learned at Harvard Business School. She is also a dating coach and matchmaker. She is a frequent guest on The Today Show and has been featured in dozens of magazines from Oprah to People. Her Web site is findahusbandafter35.com.
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