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Puzzled About Dating After 50?

Our relationship expert answers your questions

Transcript from an online chat with Dr. Pepper Schwartz

Question from Carl: I recently started dating after a divorce. What advice would you give me as far as first date suggestions? Should my courtship techniques be the same as when I was in my 20s?

Also see: A guy's guide to dating.

PS: Keep it short and simple. Meet for coffee. If it's great, then you can extend the time. If not, you have a good out. Do something where you'll have something to talk about. Taking a walk, for example, can put a lot of pressure on two people who have just met. Go see a movie, a play or sporting event.

Pepper Schwartz - Dating again?

Photo by: Ronnie Kaufman/Corbis

Finding new love is possible at any age.

Question from Jeannie from Cleveland: My 22-year-old son lives in the house and I want to date. What should I do? I feel like a teenager!

PS: You're not a teenager, so you have rights! That is to say, you are a mature woman and you want to date, so I think you need to talk to your son and tell him that you are going to start dating again. On the other hand, you don't want to put your date, yourself or your son in embarrassing situations. You might meet your early dates outside the house, or not bring them to the house unless the relationship is becoming more important. He is 22, and he has heard of "dating."

Question from Guest: Men with gray hair are thought to look distinguished. What do men think about women with gray hair?

PS: In general, I think they think they're older. I don't think it's fair, but it's probably true that gray hair is a signal to men that a woman is older and he may or may not like her ability to embrace her own aging in that way.

Some women of course look stunning with gray hair. It's the right color for them. Others not so much. But there is more to love than hair color, and I think people pick who they love on other criteria.

Question from Denise: Are online dating sites good ways to meet people?

PS: I think so. You have to try different sites to see which ones feel comfortable for you, and which ones have tools that you think will create a better chance of a good relationship. There are also sites that are primarily about friendship or finding someone to do things with. And they are good introductions to social networking, and a good way to ease into trying an actual dating site.

Next: How many dates before sex comes into play? »

Question from Leanne from Austin: What are the rules about dating and sex today? Fifth date? Third date?

PS: Well, there are people who even do first date. But I think third date it starts to up the ante, and by the fifth date there is some pressure for some sexuality. However, if you are conservative about sexuality, try and date someone who is also conservative about sexuality, and wants a deeper commitment first. One of those things that you can pick on is whether you and this person have similar values. And if waiting is important to you, I assure you there are people out there who feel the same.

Question from Randi: What do you think about long-distance relationships?

PS: I think they are hard but not impossible. They take a lot of attention, by e-mail, by phone, sacrificing money because the cost can become difficult. And it's easy to grow apart because you're not sharing day-to-day life. That said, I know people who had HUGE distances between them and survived that and ended up committed and together. So it's not easy, but if it's really important to both of you, and both of you work at it, it can have a good outcome.

Question from Lois: What about trips that are only for singles?

PS: I think day trips for singles are a good idea, or maybe even three days. But a longer trip, if you don't really find someone interesting, would be a problem if you were trapped, say, on a boat or mountaintop. On the other hand, if you went with a buddy, you could have fun even if there was nobody interesting there. So if you have a friend who will make any trip interesting no matter what, then give it a shot.

Question from Barbara: I'm currently dating a gentleman very sweet in every aspect. We both are widowed, and we have gone out, but I'm not ready to invite him into my home. What do you think?

PS: I understand your hesitation. It is very intimate to let someone into your home and it may set up expectations for a fuller relationship that you're not ready for. Still, there is an arch to relationships: They either get more or less intimate. So if you really like this guy, at some point you should open up more of your world to him.

Question from Fran in San Fran: You don't mention a lot about homosexuals dating. Why is that? Gays are people, too!

PS: I totally agree with you. It hasn't been clear that someone was asking the question about a gay relationship. But I think most of the things that apply to heterosexual relationships have resonance with same-sex relationships. Of course there are some differences, and I would be sensitive to those differences.

But just so you know, I was the lead witness against the don't-ask-don't-tell rule in federal court and I testified for gay marriage in Hawaii, and for gay adoption and foster-child placement in Arkansas. So please feel free to ask me questions that involve same-sex relationships, and I will be glad to try to be helpful.

Next: How to get back into the dating game. »

Question from Sarah: I'm worried I have too much baggage to go back out there after a couple of failed marriages. Should I just sit it out at this point?

PS: Never give up!!! Just because you have had some intimate relationships that didn't work out, that doesn't predict the future. On the other hand, if you don't think you know what ended those relationships and you don't feel wiser and more capable of a relationship now, then you should go see a therapist or counselor so you can solve some of your previous problems and get rid of the baggage.

Question from Janet: I don't even know where to begin. I lost my husband two years ago. I have dated about four men. I haven't found anyone who likes to do the same things I do since my husband. Is it possible? I am 51.

PS: Here's another idea. Join singles groups that do the activities you love. If you like to hike, you are likely to meet men who like to hike in a hiking club. If you like opera, join a group that supports opera. Almost all activities have either singles groups or mixed groups of singles and married people who are all devoted to the activity at hand. But remember, if you don't find someone interesting in the group, you should leave — don't get stuck in a place where there is no opportunity to meet someone. Remember, the ultimate goal is to meet the love of your life.

Question from Lorraine from Philly: How can I date younger men without being labeled a "cougar."

PS: I'm not going to label you a cougar! I think people should go out with the people they are attracted to. We don't call Demi Moore a cougar — we just think of her as beautiful, famous, talented, and with good taste. Of course she is stunning. But I don't think that attraction is all about how you look. It's about who you feel good with. And if you pick somebody who you feel good with, your friends will be happy for you.

Question from Stacy: I was thinking of joining a local art group that meets once a week as a way of meeting someone who shares my interests and is active — not the couch potato type. Is this something you would recommend?

PS: Yes, I think it's a great idea. You will be around someone who shares your passions, and have a lot to discuss. But just remember if it's a small group, it needs to have new people cycling in, or you won't be able to get any chance at meeting somebody important in your life.

Question from Guest: I am 59, and all of the men that I see are interested in younger women. Do I have to find an 80-year-old to be the younger woman?

PS: No you don't, although there are some great 80-year-olds out there! You can find an age mate, or you could find someone who really doesn't care about age. I don't think that all men pick on the basis of age. And quite a few men want somebody who has had life experience like their own.

Next: Find the time and energy to date. »

Question from Catherine: I'm too busy to actively date. A teenage daughter, a 60-hour-work week, a full slate of volunteer/local board responsibilities, and a garden that still hasn't been planted. Yet I can't defer romance forever. Would love some advice on how to prioritize my love life. Thanks!

PS: Let the garden go — it can come back next year. There's always a little bit of time if you look for it and prioritize. For example, clean up the house every third day instead of the second. See one less friend for lunch. Once you prioritize, other things just have to come second and third. You can go online late at night and you can use your lunch hour to have coffee with the people you meet. Just remember, if something terrible happened — let's say you had to go to a funeral — you'd find the time for it. So let's find time for happiness, too.

Question from Denise: I'm in school, working and a mother of 7- and 15-year-olds. I'm trying to find someone who will accept me and my kids. Any thoughts on this?

PS: Look for a guy who has kids. Or a girl who has kids if that is your preference. The important point is that people who have kids learn pretty quickly that they need someone who also has kids, and guys are going to look for that, too. They want someone who has the capacity to understand children's needs, just like you do.

Question from Betty: What attracts a mature male to a mature woman once the hormones have stopped?

PS: He likes her wisdom, her energy, her self-knowledge, her acceptance of him. He likes the fact that she knows who she is, and he loves it when their interests overlap. He likes that she takes care of herself and is willing to try new things, so he gets the same kind of energy he might from a younger person with the similarities you can only share with an age mate.

Question from Guest:  Did you have to learn how to date after 50? What would you suggest we don't do.

PS: I surely did. I left a marriage of 23 years and had to figure out what I wanted now, and who, and who would want me. What I suggest you don't do are the following:

  1. Don't whine about past husbands or wives, or about children.
  2. Come to the table with happiness and a positive attitude; don't bring your worries.
  3. Don't feel you have to tell this person every bad thing about yourself. They don't need to know until there's enough evidence that things could get serious.
  4. Don't get discouraged right away. I've had people go out on three dates and say they aren't going to do it again. That's nuts. If you go on enough dates, you will find somebody, so don't quit too soon.
  5. And most important, don't forget to listen. You don't have to do all the tap dancing. She/he should get a word in edgewise.

Next: Is it OK for a women ask a man for a date? »

Question from Lois: What about a woman asking a man out for a first date?

PS: If the guy is really secure, he will like it. But some men are still traditional and they don't. So you have to ask yourself if you are willing to miss a few people and maybe that's a good thing, if you are a person who doesn't like tradition and wants to find somebody who doesn't go by those old scripts. One question: Even men who like you asking them out don't want a woman to do all the asking. Once you've asked him out, wait for him to ask the next time.

Question from Roger Dodger: Is taking a woman to a sporting event a good first date?

PS: It's a good idea if she likes sporting events. Ask her and make sure she's not just trying to be nice. Find out if the event you like is really the one she likes. And if she does, it could be a great first date.

Question from Liz: How do you find a good online dating site? The ones I have tried seem to attract men who want sex up front and act like they are back in college. Any tips for writing a good profile to attract the right guys?

PS: Go to Google, Yahoo or Bing and type in "online dating." You will get a long list of candidates. Go to the sites and see what they use as a way to present yourself to others, what the site looks like — does it look like it's intended for your kind of person? Try a few, because you won't know which ones are good for you until you've been there a little bit.

The profile is very important. Look and see which sites will help you write it, because some of them will. Also, have a friend nearby when you are writing and see if they think you are doing yourself justice, or if you are writing up something that is a real turnoff. We are never objective about ourselves, so we need people to help us.

Question from Janet: I come from a small town where most everybody is married or has younger kids that grew up with my kids. I have been widowed since 2008. I have met five men and all they want to do is stay home. I like to go to the movies, out to eat, ride around listening to good music. Is there any help for me? I am a healthy 51-year-old.

PS: What's wrong with the men in your town? What's the next town like? Go poach! There has to be somebody there who wants to get off their butt. But also, you don't have to wait for a guy to do the things you are talking about. Find some friends and do some of those things with a buddy. That ought to help until you find Mr. Right.

Question from Bonnie: I am a widow, 64 years old. I recently met a man (64) and a widower of just one year. He and I were married to our college sweethearts. He wants to remarry and doesn't want to be "alone." We've been seeing each other for over five months. He is "married" to his home, land, furnishings in the mountains, and I have a condo at the beach. This sounds ideal, but I am not crazy about his home in the mountains, and he has no interest in moving. Bottom line: I would be the one making all of the changes. Our lifestyles are different, too. Any ideas of how I might get him to stretch his ego and bend a little?

PS: You've only been seeing each other for five months. Give this relationship time to deepen. Give it at least another six months. Sometimes it takes years before people realize, or change their opinion, about what compromises they are willing to make. Just enjoy each other. Don't push it, and see what each of you can find in each other's lifestyle that's fun. Plus, in today's world, you don't always have to live in the same spot. You can go back and forth and still have a committed relationship.

Next: Will social networking help find me a date?

Question from Laney: What is the best way to communicate with the technical explosion? Facebook, Twitter, e-mail, phone?

PS: Pick some technology that is easy for you and forget about the rest. You don't need to tweet. You can live without Facebook or for that matter texting. But if you try them and one of them feels good, they can be a great way to connect.

Question from Leigh: I have a problem with a guy who says he loves me and wants to be serious. He is suffocating me and I don't feel the same way about him. How do I get him to back off? I just want to be friends, but he is making that impossible by wanting to hug and kiss. He has been a widow since last year. He was engaged to another woman in February of this year. Something just is not right.

PS: You seem very clear about how you feel about this guy, and he seems determined not to get the picture. So, sadly, friendship is probably not possible ... at least right now. You have to tell him goodbye in as nice a way as you can but firmly.

Maybe after enough time goes by, he could actually be a friend. But that's not possible right now.

Question from Laura: I am 65 and have never been married. I have trouble answering, "Why haven't you gotten married?" Any suggestions?

PS: I can't help it: So why haven't you gotten married? Just kidding! So what you need is a conversation stopper. Pick one: I'm not married because I'm the unluckiest/luckiest person on earth. Or I haven't been married because I wasn't ready until now. Or, why does everybody have to be married. Or finally, what's it to you. Seriously, the only person you have to explain that to is someone you're interested in who wants reassurance that there is a possibility of commitment.

Question from Me: Are there any men out there that would just like to be good friends?

PS: There have been books written on this question, and certainly movies (When Harry Met Sally). I think there are men who are able to be good friends without any other agenda, but you both have to be interested in each other without even a tinge of sexual attraction. But this happens. And there is no reason why there can't be an intimate friendship that is the equivalent of a friendship.

Question from Mark: I am on Social Security disability and belong to two dating websites, but I have absolutely no luck with finding a date. To me being good friends is hard; most men like myself want a more permanent and sexual relationship.

PS: I think most of the people on sites are looking for a romantic relationship. I think you might want a friend to look at the way you present yourself (your profile, etc.) and see if it's getting in the way of you finding someone. For example, you opened your e-mail to me with the fact with you're on disability. That's not a good opener in a romantic e-mail. You don't have to lie ... but you don't have to make that your introduction. Get to know somebody so they see you as a person and like you, and then you can tell them some of the facts of your life.

Thank you all for coming to this chat. I wish we had more time, and we will do this again soon. In the meantime, go to to submit more dating questions.