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Dating the Second Time Around—Don’t Let These Common Fears Hold You Back


Please scroll down for the Facebook chat with Sandy Weiner on dating over 40…

If you were married for many years before losing a spouse to death or divorce, the prospect of dating again may seem intimidating. Yet with patience and persistence, you can find a wonderful partner—and enjoy the search in the meantime.

Common fears about dating and how to overcome them…

FEAR: “I’m too old/unattractive.”

REALITY: Age need not be a barrier to meeting someone new—it even can be an advantage. At this stage in life, you likely have developed many sources of fulfillment aside from romance, such as an established career or hobbies that you are passionate about…as well as clarity about values and what matters most in life. Self-knowledge and the confidence it brings can make you radiant to the opposite sex.

As for attractiveness, you don’t need classic good looks to appeal to the opposite sex. Health and vitality are powerful attractors. To project these qualities, get regular exercise. Walk with your spine long and your head high.

You also may want to consult an image consultant or department-store personal shopper to update your style. Whatever your body type, contemporary clothes that fit well will help you project a radiant image—and this goes for men as well as women.

FEAR: “I’ll put a profile on a dating Web site, and no one will be interested.”

REALITY: The 50+ segment is the fastest-growing group on dating Web sites. It should be a part of everyone’s dating strategy. You can take simple steps to improve your online dating success and capture the attention of interesting people. Keys to success online…

Register with more than one site. To increase your exposure to people who might be a good fit, start with two sites. One should cast a wide net, such as or The second should be more specialized, such as (for Jewish singles), (for Catholics) or (for people over 50).

Show, don’t tell. Don’t post a list of interests and adjectives about yourself—everyone does that. To stand out, tell brief stories about those qualities. Example: Instead of vague phrases such as “love to travel,” describe what inspired you about your most recent trip.

Ask friends what they see as your top five characteristics and for vignettes that illustrate them. Incorporate these examples into your profile.

Post current photos. Choose four or five current photos that look like you and that show you at your best. The main profile photo should be a close-up of your face. The others should show you in a variety of poses doing things that you love. If you don’t have recent photos, ask a friend to take some.

Don’t wait to be discovered. If someone’s profile interests you, send him/her a message through the site. This applies to women as well as men—it is perfectly acceptable, and expected, for women to contact men on dating sites.

Make your message short, catchy and specific. Mention one or two things in the profile that made the person stand out for you, such as a warm smile, a clever turn of phrase or a book title.

Don’t be discouraged or take it personally if your message doesn’t receive a reply—it happens to everyone. Keep viewing profiles and contacting new people who interest you.

FEAR: “I may put myself in danger.”

REALITY: You should take simple, sensible precautions to protect yourself…

Protect your privacy. Don’t use your real name as your screen name—instead, use a hobby or personality trait, such as FilmFan or LoveSailing. Have a separate e-mail address that you use only for online dating messages. Don’t give out your phone number until you have built up some rapport and trust via e-mail, and use your cell phone so that the number cannot be easily traced to your home address.

Whether you become acquainted online or through more traditional means such as a friend or a class, choose a public place for your first few dates. Tell others where you will be. Don’t get picked up or dropped off at home until you have known the person for a while.

Do some checking. As soon as you know a prospect’s full name—which usually is early in the e-mail stage—do an online search to determine whether he has portrayed himself accurately. In addition to searching by name, you can copy his photo into a search engine such as Google Images and perform an image search. By using this technique, I learned early on that someone I had met online had disguised his identity, made up a sob story and asked a number of women for money.

FEAR: “First dates will be awkward.”

REALITY: First dates can be awkward, but they also can be interesting and fun. Although meeting for coffee is a classic, low-key first date, consider more active options such as visiting a museum or taking a walk downtown. Standing or walking side by side is less awkward than sitting face to face, and your surroundings will provide conversation cues.

In addition to talking about mutual interests, ask lighthearted questions that delve beneath the surface. Examples: What was your favorite toy when you were growing up? What would you love to do if there were no constraints? What’s the best advice anyone ever gave you? If your house were on fire, what’s the first thing you would grab to save?

FEAR: “There are a lot of losers out there.”

REALITY: More than any other factor, your attitude has the biggest impact on your satisfaction with dating and your ability to meet compatible people.

Television and other popular media reinforce negative stereotypes of the opposite sex by portraying single men as inept or self-centered and single women as confusing or impossible to please. But these are just caricatures.

The truth: Many men are capable and loving. Many women are straightforward and agreeable.

Assess a person’s character by paying attention to the person’s actions as well as words. Look for evidence of kindness, respect, integrity, emotional generosity and responsibility.

Examples: Does she show up when she agreed to or keep you waiting and make excuses for being late? How does he treat the staff at a café? Does she put her cell phone away during dates and give you her full attention? When the subject of past relationships comes up, does he dwell on his ex’s negative traits?

FEAR: “He/she will want sex right away.”

REALITY: Plenty of people don’t mind waiting, and someone who is right for you will respect your boundaries.

If you are interested in someone but this person is getting more physical than you are comfortable with, express your feelings frankly in a positive, nonjudgmental way.

Examples: “I’m attracted to you, but I want to slow this down”…“I don’t have sex with someone this soon, so for now why don’t we just kiss and cuddle.”

If and when you are ready to have sex, make sure that both of you have been tested for sexually transmitted diseases. Not only is this important for your health, it also is a good gauge of your relationship. If you don’t trust each other enough to show each other your test results, you’re not ready to have sex.

Bottom line: The biggest obstacle to finding love in midlife or later is staying home. So move those fears aside, and get out there and date.

Dating Over 40

How to find love this year

In a Facebook chat with Bottom Line/Personal readers, dating coach Sandy Weiner, Chief Love Officer and founder of Last First Date, answered common questions about dating when you’re over 40. Here, her helpful and inspiring advice…

READER:   What do you think about online dating? I’m over 40, are there specific sites you would recommend?
EXPERT:   Online dating is a must if you want to meet people over 40. It should be part of a 3-pronged plan: Socialize with other like-minded singles in person, effectively ask for setups, and date online. I would recommend two sites; one large site like and another smaller niche site such as,, or one for dog or cat lovers/apple lovers…there’s something for everyone!
READER:   What are your preferred dating web sites for 60-year-olds?
EXPERT: is good, as well as the big sites like You should check them out and see who’s on the site before joining. Everyone has different preferences, and people find love on all of them.
READER:   Any advice for friends of singles on the best ways to set them up? Or is it a big mistake trying to set up single friends?
EXPERT:   I love this question. So many people ask for setups in ineffective ways. It becomes a random ‘boy meets girl’ with nothing in common setup. Or, more commonly, the friend will say,’ I think you’re amazing. I wish I knew someone great for you, but I don’t.’ Ask for a setup by connecting with a friend or two who are great ‘connector’; they know tons of people. Meet them for coffee or lunch and tell them you’re serious about finding love this year. Then brainstorm with them. ‘Sally, your husband works out at LA Fitness, right? Maybe he knows some guys from there. You work at a law firm. Any men there that might be a good match for me?” Plant seeds. And tell your friend the top five ‘must haves’ that you need in a partner. You’ll have much better luck!
READER:   I’m a 47 year old divorced woman and find that men my age are interested in women who are so much younger. Why don’t men want to date women their own age?
EXPERT:   Ah, the age old question about men dating much younger women. My father is 92 and is interested in women who are 55. Some men equate youth with beauty. It also makes them feel that they still have it going on. To that, I say who cares? You can’t change those men. What you can do is realize that there are many men who love women their own age and older. An evolved man will think a woman his age or older is hot and sexy. Focus on those guys, and let the other men have their bimbos!
READER:   The men I’ve gone out with are way too ready to be sexually intimate. How can I delay without men losing interest in me?
EXPERT:   If you are attracted to a man and you’re not ready to have sex, let him know that you need to pace yourself. But make sure you also tell him you’re attracted to him. I believe that if you’re serious about finding a long term lasting relationship, you should probably wait to have sex when you are exclusive. Say something like, “I think you’re very sexy and I’m attracted to you. I don’t have sex with men until we are in an exclusive relationship. I’m not rushing this at all. But if and when we’re exclusive, you’ll be in for the night of your life.” That should keep him very happy…
READER:   How can I cut out of a date early when I know that it’s going nowhere? If you suggest sticking it out, how do I make the rest of the evening bearable?
EXPERT:   A first date with a stranger should be short and sweet. Coffee/tea, a walk through a museum, a walk in a public place. If you’re only meeting for an hour to 1 1/2 hours, how intolerable can it be? If you really can’t bear it, say that you have to go. I also suggest that you find a way to make it more bearable by asking good questions and looking for something positive in your date. I believe every date is a learning experience. Go in with a great attitude and you’ll have a much better experience.
READER:   This has happened to me and I regret later I didn’t ask a good question. What are some questions that will get the other person to respond? Something that is fun and will lighten up “things.”
EXPERT:   A great question would be something that gets him to talk about his childhood, like, what was your favorite toy growing up? What sports did you play as a child? What was your favorite vacation and why (the why will give you info on his values). If you could quit your job tomorrow, what would you do? What’s one thing about you that I wouldn’t know from looking at you? Do you have a secret talent?
READER:   Do the rules of dating change now that I’m over 50? In particular, do I really need to wait a few days after a date to schedule another when I like someone?
EXPERT:   Rules, shmules. I believe in principles, not rules. But there is some wisdom to waiting. The point of waiting a day or two is that if you seem too eager, you run the risk of scaring away your date or appearing to be needy or someone without a ‘life’. Your value goes up when you don’t appear too eager. That’s during the courting phase. Once you’re in a relationship, you can both chase each other.
READER:   I’ve been a widower for many years, but I’m ready to start dating again. When I tell women this (because I don’t want to lie), I can tell that they pity me. Should I avoid full disclosure, until they get to know me better?
EXPERT:   I’m sorry for your loss and happy that you’re ready to date again. Women pity you? You, my friend, are a hot commodity. Women who date widowers feel they’ve hit the jackpot! A man without baggage! Whoot whoot!! On a more serious note, if you don’t monopolize the date with sad stories about your deceased wife, the woman dating you will fall for the man sitting across from them, not a man they feel sorry for. I’ve dated widowers who were not yet ready to date, and I’ve said no thank you to date number two. But, you’ve spent time healing, so you are ready to jump into the dating pool. Have a great time!!
READER:   I look young for my age, am very active, and would like to try dating younger men, but they get scared off when they find out my real age. Should I withhold the truth until they know me better?
EXPERT:   I was a firm believer in not lying about your age until recently. I also look young for my age, and when meeting men in person, much younger men will approach me. And it’s rude to ask a woman her age, isn’t it? So, I do think it’s okay to lie about your age if it’s just by a few years when dating online. And do come clean on the first date. The purpose of online dating is to get OFF line.
READER:   Should a red flag go up if I meet someone in their 40s–or older–who has never married?
EXPERT:   I believe that you should not jump to conclusions about why someone has never been married. They might have been in a long term relationship and know how to be a good partner. Early forties is not as critical as late 50’s and up. My concern is that if you were married and had kids, your life experience won’t match theirs. I would get curious, not judgmental. Don’t write them all off as relationship-challenged. Take each on a person to person basis.
READER:   How much should I talk about my children on dates? They are very much a part of my life but I don’t want to be boring, either.
EXPERT:   There’s a time and a place for discussing your kids in depth. When you’re on a first or second date, focus on your date, not your kids. You can mention their ages, what they’re up to in life, but that’s it. If/when you’re in a relationship, you’ll want to share more about them. And please don’t say that your kids are the most important people in your life. That’s understood, but will give the impression that your date is ‘chopped liver’.
READER:   My children are grown. How important should it be that they like the people I date? Of course new partners need to get along well when children live at home, but once they are out of the house, can my new relationship work out–even if they don’t get on so well?
EXPERT:   My feeling about grown kids is that you need to please yourself before worrying about pleasing everyone else. If you’re truly happy and you have a great relationship with your kids, you should be able to talk about any issues that arise about your new significant other. If there is terrible conflict, it won’t be great for the relationship, and you don’t want to have to choose between your kids and your mate. But communicate and listen to your kids at any age, and you should be able to work things out.
READER:   Could so much online dating be giving people too many choices?
EXPERT:   Yes, for many people, the overwhelming amount of people to choose from can make for either overwhelm and shut down, or a lack of commitment. However, if you’re serious about finding love, you can narrow your search in your preference settings, and the choices will be less overwhelming.
READER:   I’m a single woman again and the often-mentioned M/F ratio really depresses me. Is it true?
EXPERT:   It depends which study you’re looking at, where you live, and how much you care about statistics. In my opinion, you’re looking for one special person. That person can be 1 in a million or 1 in 10. Does it really matter? Some dating sites have more men than women; some have more women than men. I say dump the stats and date like you’re a very special person looking for a special partner. You’ll find him or her.
READER:   I’m in a relationship now where the man I want to marry talk and texts his ex 2-5 times a day sometimes. He has two children with her (15, 18 yrs. old) He states they only talk about the kids. They live within a mile of each other. She is 20 yrs. younger than he is, and they buy each other gifts roughly worth $100-$200. He thinks I’m being unreasonable that they should stop the gift giving the gifts and talking so much. They say the gifts are from the kids, but the kids don’t even know what the gifts are.
EXPERT:   You say it’s the man you want to marry. Has he asked you to marry him? If so, you’ll want to work this out before you get married. Mutual respect and trust is a cornerstone of a happy relationship. From what you’ve shared with me, his texting and gift-giving seem excessive. There is such a thing as a ‘bad divorce’ where two people who were married haven’t fully disconnected. Make sure he’s not one of those… Good luck!
READER:   Is there individualized dating coaching available for a twice-divorced, 60-year-old heterosexual male?
EXPERT:   Many of my clients have been divorced more than once. I feel that if you are open to taking responsibility for what you’ve contributed to the failed relationships and are willing to learn effective dating skills, I can work with you to find love.
READER:   I’m a 55-year-old woman, recently separated, and am living overseas. I’m having a hard time meeting people, and am having trouble accepting my age. Do you have any advice for me?
EXPERT:   If you’re recently separated, now is a great time to fall in love with the new you as a single woman. It’s important to regroup and find out who you are after a marriage ends. When you say you are ‘having trouble accepting your age’, it sounds like you are not embracing your whole wonderful package. You are beautiful and wonderful at any age. Find a hobby that you love, and learn to spend time alone before looking for a partner. When you start dating, you’ll attract a much higher quality partner who matches your self-esteem.
READER:   I am in a relationship with someone whom I love dearly. He has talked about getting married and has 3 children of his own. I have never wanted children of my own. What can I do?
EXPERT:   Would you be okay with his children? Have you discussed that you don’t want children of your own? If that’s a deal breaker for you, you can’t marry him or you’ll be miserable. If you’re okay with his kids and he’s okay with you not having more kids with him, congratulations! Enjoy married life.
READER:   What do you think about long distance relationships? Can they work?
EXPERT:   Long distance relationships can work if both partners put the effort forth. With Skype and Facetime, you can see each other every day if you like and stay connected and close. Make sure to schedule in time to get together every few weeks. If neither of you can travel, it can become a problem. With mutual effort, long distance relationships can be amazing. Make sure at some point you spend significant time together to see what you’re both like. Short visits are different in nature than longer ones. Good luck!
READER:   I am dating someone who is much younger than me. In fact, he is closer to my adult daughter’s age than my own. I don’t see age as a factor in our relationship and neither does he. If my children are okay with this, should I worry about what other people think?
EXPERT:   If you two love each other, I feel that age is irrelevant. You may not get the same pop references, but if that’s okay with you, then go for it. One of the blessings of midlife is that you stop caring what other people think, right? So, stop caring and enjoy each other.
Source: Sandy Weiner, dating coach, blogger and workshop leader who specializes in helping people over 40. Based in Stamford, Connecticut, she is chief love officer at, where she has posted many articles about dating in midlife. She hosts the online radio show Courageous Conversations at Date: March 15, 2013 Publication: Bottom Line Personal
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