Dating After 50, Insights from Dating Coach Peggy Wolman

By Lu (Jenny) Xing

March 25, 2015


Peggy Wolman runs a business of matchmaking and dating coaching for people of all ages in Boston, Massachusetts. Being an older woman herself, she is well known for her work with women who are actively looking for love after the age of 50.


Could you tell me a little bit about your dating coach experience and your clients?

Half of the clients who come to us are over the age of 50, and half of those are women. Those are women who have not given up hope that there is someone out there for them, even though they are older adults. They are either recently divorced or widowed, or in some cases, never married. And they just don’t have the strategy and skills that they need to get back to dating after 20 years, 30 years since they’ve been dating again. So we try to teach them skills and strategies as a coach.

It’s basically a three-month program to guide every woman, every older adult, to have an online profile and we write online profiles for them, do professional photographs, and we are there as their mentors through email or phone conversations to talk about meeting men, going out for coffee, and going on dates and how to develop a meaningful relationship. That’s pretty much what we focus on in terms of dating coaching.

There is matchmaking as well, but that’s not as much for women. That’s for men. We do make some introductions for women. People can join our membership, and become free members. They are in a database. If we have a male client and think they might be able to match, we will call for a meeting of three and make an introduction.


So for most clients, you are helping them with online dating?

Yes, it’s mixed. Everybody should go online. Every woman should go online whether or not they have a matchmaker, because a number of people are online, millions and millions of them. You would have many opportunities to meet many many more people. You really need to cast your net as wide as possible and that’s the best way to do it.


What online dating sites would you recommend older women to use?

We definitely recommend We recommend OkCupid. Some women like eHarmony. There is an older women dating site called Ourtime, which is also owned by It’s hard to generalize, because for whatever reasons, women are successful on different sites. Some women who have strong religious preferences might want to go on ChristianDating site. You know, there is petlovers, there are thousands and thousands of dating sites that are out there. So we suggest trying to go on a few.

We also do a lot of the vetting part for them, so if they are not comfortable on how to search the people that they would love to meet, that’s part of the service that we offer.We go on the site, log in as them, and we vet for them, so we help them choose the people that maybe best for them to meet, because a lot of women are nervous about it, you know, they are not sure if they are making right choices or whatever.


How do you help them find someone matching their needs?

I think, first, they should think about what they can bring to the table, not what they need. Who are they, what makes them become someone that men want to take out. That’s the first thing they need to feel comfortable with. They need to really figure out who they are, not what they do for a living, but who they are. Women are very good at talking about what they do, but not good at talking about who they are. Then we can talk about the kinds of person that they may like. Who are the kinds of people in your life that make you happy, what they like, what kind of girlfriend you have, and what is her personality. What are the kinds of people that make you happy, not what you think might make you happy. I have some clients saying I have to find somebody who likes water sports, I have to find someone who has a graduate degree, I have to find somebody who is very close to his family, then they may have a close friend who doesn’t do anything in water sports, who is not close to her family, but they have a wonderful relationship together. So a lot of the things that they think they need are not important at all.


You mentioned among your clients are women who are recently divorced, some who have never married. What, if any, kinds of differences do you see in the coaching needs of divorced women compared to never married women?

Everybody has a lot of baggage whether you’ve never been married or you’ve been divorced. Women who come out of divorce have a lot of trust issues. So regaining trust in people again after they lost the trust in the person that they lived with. For women who never get married, the issue is to trust anybody to start with. It’s not that dissimilar, but it is different because I think you are not making a comparison to a prior relationship. That’s also true for widowed women. Some of them have lost their spouses, and they really had a wonderful relationship, and need to accept the fact that they may not be able to replicate that relationship, but what would a different relationship look like for them. Baggage from divorce is different from baggage from widowhood or never being married. But they all come with hope, and they all come with maybe something will work better this time than last time. I think they will do much better when they are trying not to experience this alone. They need a coach in their corner, someone to turn to, and ask questions.


What kind of questions do they usually ask you?

Everything from, you know, how come the only thing he wants to talk about is his children? How can a man just want to talk about his ex-wives? They want tools to be able to change the topic and the conversation, like how do you make someone talk about himself, not about his prior life.They want to know who should pay when they go on a date. They want to know when they should think the relationship is exclusive, what if the man does not want to commit to an exclusive relationship, and should they continue to date? They want to know when they should meet each other’s children. They want to know if they still have a relationship with their ex-spouses, how accepting should they be of that, and how much should that enter into this relationship…. Endless amount of questions, you know, just how to move forward. How to figure out whether or not this relationship is a good relationships very hard for every person to do when they haven’t done it for 20, 30, 40 years. A woman aged 50 could have been married for 20 or 30 years and never thought about ending a relationship.


In addition to all those concerns about men, do women have any concerns about themselves? Like do they worry that they are less attractive because of their age?

Not as much. I think by the time they come to us, they think they deserve to find love again. Most of them are past that phase. They think OK, I made a mistake,I had a bad marriage, I know what a bad marriage looks like, and I want a good one.


What are some other concerns that older women have when they date?

They want to create a trusting and loving relationship, but they don’t know how to do that step by step, so having someone to coach them through this process, helping them get more comfortable expressing their feelings, so if someone says something that they don’t like, they have to be able to talk about it.


What tips do you give to them on that?

In general, just to say, if somebody says something that troubles you for whatever reason, you need to be able to say, you know, I’ve been thinking about what you said, I need to tell you that I didn’t feel comfortable with the comment you made about whatever, and I just want to let you know that. Some guys can understand that, while others cannot. But that’s how you understand if you can talk about feelings together. If you can’t talk about your feelings, you are not going to have a good relationship.


Do you feel you need to empower older women, so they can be more confident?

Yes, exactly. Older women are hoping to find a good relationship again. They have to believe that people will like them. Because one marriage or even two didn’t work doesn’t mean that they can’t find someone to share a meaningful relationship with. I think confidence comes from having them be prepared. So one of the things that they need to do is to get prepared before they go on a date, to be their best self on the date, to not talk about negative experiences in their life, and to make every day as interesting as they can. There is always something to learn from everybody. Have them try to enjoy an interesting experience. Do not decide whether you are going to like this person or not, just decide whether you enjoy this person or not, and being able to articulate why.


You mentioned half of your clients are older women, the other half are younger women. What, if any, kinds of differences do you see in the coaching needs of older women compared to younger women?

Well, when you are younger, when you fall in love with someone, you really fall in love with the potential of a person. You don’t even know what they are really going to be in their life. It’s all about excitement and hope. But, you know, by the time you are an older person, you are not really about their potential, and they are not about your potential, you already are a developed person. You are making choices based not on what they are going to be, but on who they are. And when you are younger, you have sort of fantasies, your expectations are built on fantasy, not built on reality, just what you hope marriage will be like, or what life will be like, or what having a family will be like. When you keep marrying and getting divorced, get married and lose a spouse, whatever, reality becomes a history.You have this history, and you have someone else’s history too, although they are very very different histories. You have to decide how much the history matters, and how much the moment, today, matters, because these people come with a history, you won’t be able to share your history with them. They are really interested in going forward. Things are different for older women who have life experiences. They know much more than younger people, which also can be much more painful.


Do you have any final advice for older women?

I think older women should not give up hope. Love is a valuable part of life. It’s a terrific project. They need to be proactive. They need to be an active participant. A 60-year-old woman today can look like a 30-year-old. Do not let age be the determining factor. I always like the quote “How old would you be if you didn’t know how old you are?” It’s a Satchel Paige quote, a terrific quote.