Dating After Divorce: Guide to Online Dating Over 40 (or 50, or 60)

Are you recently divorced, and curious about online dating?  Or, have you been at it for a long time and starting to wonder why it's not the dating wonderland that you thought it would be?

This post is based on the experiences of my divorce recovery coaching clients over age 40, and my opinion of your potential for online dating success depending on what you want from a relationship or an encounter with a man.

As a multi-year veteran of online dating sites, and someone who has informally crunched data on women's online dating experiences at a variety of ages, here's the best (and, I hope, the most helpful) of what I've learned.

The subheads below reflect the desires and mindsets that I hear most often from the women I work with, along with my subjective opinion on how successful online dating may be for each group of potential daters.  Some women have more than one of the following deep desires, but in most cases, there's one big one that motivates them to take their search online.

I can't stand to be alone.

Does this describe you?  You say things like, "I can't stand sleeping in an empty bed," and "It's so depressing to come home to an empty house."  You're an easy-going lady who doesn't ask much from a relationship, and you're happy that way.  You just feel you need companionship, and "need" is the important word.  It's not just a wish, or something that would be nice.  You don't feel right without a guy in your life.

Potential for online dating success:  You're the woman online dating was made for, and you have a wonderful chance of success with it, if you create a profile that draws men in your preferred age group.  (More on preferred age group later on.)

I just can't help but suggest:  If you're easy going and easy to please, that's wonderful -- and it's what most men are looking for.  But, please be sure that you're receiving what you need in a relationship.  If you tend to use the word "empty" to describe your life, try exploring other fun actvities to fill the void before turning to dating.  If you feel that any guy is better than none, I would love for you to know that you are special and you can ask for more, if you want to.   

I just want a sex partner.

Does this describe you?  You feel like you're going crazy without a sex partner.  Sex may not have been part of your marriage for a long time, and you wonder if you're still desirable -- and you may feel the need to prove this.  Or, maybe you have nothing to prove.  You just want sex, and are not afraid to say so.  Maybe you're not at the place where you're open to a relationship at all.

Potential for online dating success:  You can be having sex within 24 hours.  Say what you're looking for in your profile, in a subtle way, and men will be crawling out of the woodwork.  Be careful of being too obvious because this will bring out men who can be more than you bargained for.  I've never met a man online who wasn't upfront about sex as highly highly highly important to him,  so be ready for some messages in your inbox that might be pretty direct.  

I just can't help but suggest:  If you can have casual sex with someone who is already a real-life friend, this can be so much safer.  If you choose to use online dating for this purpose, please be very careful.  And, please don't pursue this, if you have children.  Do not allow any of these men to know anything about you:  No phone number, no address, nothing about where you work.  And, please use condoms every single time.  They won't want to use them.  Too bad.  So many women contract HPV and worse this way.  

So many of my clients tend to jump into bed on the first online date, and are crushed when the man rejects them or continues to use them as just a booty call.  Please be careful on all counts.  You may think you just want no-strings-attached sex, and find out that you develop feelings for someone who sticks with the original program.  This has happened to many of my clients and it ends up as a terrible hit to an already fragile sense of self-esteem following divorce.

I need someone who "gets" me.

Does this describe you?  Friends say you're picky simply because you want more than someone with a job and a pulse.  You need to share at least a few important interests in common with a man in order for the relationship to be fulfilling for you.

Potential for online dating success:  On the face of it, you would think that online dating is perfect for you.  You can get an idea of a guy's interests by reading his profile, right?  Then, all you have to do is find each other.  Well, yes and no.

In order to have a larger pool of guys who may respond to you, I suggest the following:

  • Don't wait for men with your interests to contact you. Do send them a brief message mentioning what you have in common.

  • When they reply (which they will, if you are physically what they're looking for -- looks are almost always #1 in the male mind), don't exchange emails forever, and don't get on the phone. Suggest a brief meeting for coffee. You don't want to waste your time getting to know someone who's just a voice and a fantasy, and after weeks of long phone conversations, find out that the man, in person, leaves you cold.

  • If you're over 50, consider using dating sites exclusively for mid-life daters, and also consider shaving as many years off your profile age as you can get away with. If you meet someone you like, do not talk about age until he has gotten a chance to know you, and when you do come clean, explain why you took that step with your profile. To learn why I suggest this, please keep reading the next section about women over 50.

I just can't help but suggest:  Don't leave your romantic future up to online dating.  Pursue your interests and find ways to meet, in person, men and women who share those interests and passions.  The women you meet may know someone perfect for you.  Plus, the more you date, the more you will understand that happiness in life can be a lot more about friendship and connection than about just one guy.

I'm age 50 or over, and I want to be with a man my own age (or younger). 

Does this describe you?  You spent the best years of your life (so far) taking care of your ex and being deferential to his wants and needs, and you really can't get too excited about starting over with a much-older-than-you guy who's not in good health, or prefers to watch TV every night.  You've noticed that even most men in your age group aren't as healthy and active as you are, and aren't sexually attractive to you.

Potential for online dating success:  Not so much.  Men typically search for women 10 to 20 years younger than they are because they don't feel they can be sexually attracted to women their own age.  So, if you create your profile using your real age, you'll tend to turn up only in search results of men much older than you.  And, if you make the first contact, men may take a look at your age and simply ignore you.

It's theoretically possible to find someone nice online to spend some time with, but how many hours do you have available to put into the search, and to meet problem guy after problem guy (economically struggling, chronic health problems, unsocialized, or with problem children who would impact your life as well as his)?

Across all male age groups, a successful, attractive older man has the most choice.  And sad as it is to say, he most most likely won't be choosing a woman remotely close to his own age unless she outdoes him in every department (looks, wealth, social position), and even then, he'll probably try for a woman 20 years younger who still outdoes him in almost all of those departments.

I just can't help but suggest:  If you're an older woman, it benefits you so much to meet potential dates through traditional channels -- church, meetup groups, volunteering -- because, this way, age doesn't even come into the discussion until you've gotten to know someone a little.  If you truly look young for your age or have a bright and happy personality, you get to play to your strengths when you meet the old-fashioned way.  No one is asking your age, profession, or income level up front.  Maybe you're not exactly the type he's looking for, but you're so friendly and nice that he can't help but like you.  Men get to simply meet the real you, and find out, in person, how great you are.

Meeting real, live people, the old-fashioned way, is the best-kept secret of the decade.

My advice for any divorcee getting back into the dating world is to gradually build into your life more ways to meet people -- new women friends as well as new men friends.  Get involved at your kids' schools, go back to church if you're a person of religious faith, volunteer where you're likely to meet men.  Get creative.

The advantage of doing real activities with real people is that it will make you feel like you're part of something fun and you won't feel so alone.  As a newly single woman, you'll get used to interacting with men and feel more relaxed about pursuing online dating (if you decide to do so).  It's so much better when online dating isn't the only game in town, and you can feel more "whatever" about it.

Odds and ends . . .

Don't try too hard.  Don't let your ears visibly perk up when you see an attractive man without a wedding ring.  Just be friendly and nice, and move on.  Lather, rinse, and repeat.  Always be friendly, but don't start delivering casseroles to his doorstep : )

Choose the right dating site for you.  Take care in choosing a dating site that attracts men who are looking for the same type of relationship.  Be aware that the big dating sites (, OKC . . .) work best for women in their 20s and early 30s and the power shifts to the men from the mid-30s and up (while the choice of quality men declines as age increases).  There are all kinds of niche dating sites for different age ranges, religions, professions . . . you name it.

Don't give in to more intimacy than you want.  Know that men (especially on dating sites) will often be relentlessly pushing you for sex as soon as they can get it.  If that's not your wish, too, have a conversation and explain what you're looking for in a relationship.  I read somewhere that men think of sex as trying to figure out whether you're a candidate for a relationship, whereas many women think having sex means they're in a relationship.  Don't be fooled.  Don't be hurt.  

You have the power to say no.  If he doesn't understand, you haven't lost anything important.  (Men want to make sure that a woman likes and wants sex.  But that doesn't obligate you to do something you're not ready to do.  Just because he's not as bad as the others you've met doesn't mean it's time to give in -- unless you're happy with that decision.) 

TMI.  Please don't give someone your phone number or address, or let him pick you up from home or work when you really don't know him (even if you know a little about him, for example, his address or where he works).  Sensible men will understand why you want to protect yourself.

Married men are on dating sites pretending to be separated or divorced, so do be aware of this.  It's another reason not to jump into bed with someone just to keep him around.  Until you have known a person for a while (a couple of months, at the minimum), he won't be letting his skeletons out of the closet (whether it's that he's married, or comes with some other deal breakers).

Keep it casual.  If you are looking for a serious relationship, do wait as long as you possibly can before getting physical with someone.  Don't allow him to turn up the heat, or to see you more than a couple of times a week.  If you keep it casual, over time, he'll allow you to see sides of him that weren't in the dating profile:  He may be married, he may be involved in another relationship or two, he may have a very serious health issue, he may be heavily in debt, or he may have a mental, emotional, or substance abuse problem.  Or, he may just be a perfectly nice man with just the average, garden variety pros and cons to him that we all have.

Treat each person as a potential friend.  If you keep it casual for at least a couple of months, you can get to know each guy as a potential acquaintance and friend, and not worry about whether or not he's a potential life partner.  This way, you have no need to grill him about your deal breakers and scare the heck out of him.  Just as with people you meet in real life, you do get to know who they are over time, in a natural way, and you don't need to emotionally and physically involve yourself in a hurry.

Be ready for this to be a part-time job.  There's someone for everyone, and what's a red flag for one woman will be perfectly acceptable for another.  All I'm saying is, please be ready for a long slog, and many first meetings that go nowhere. That's why what I'd really like you to take away from this post is:  Don't pin all your hopes on online dating.  Get out and meet people.  Practice talking with guys -- without the pressure of a first date.  

Just be your own beautiful, human self and start feeling great about meeting new friends.  This way, your social life will bring you an ever-widening circle of fun and like-minded friends.  No stress.  No fear.  Just fun -- and maybe a new man or two in your life.


Enough Said: Is he "good enough"?

As I wrote my July 11 post, "Are Men Really More Attractive as They Age?", in the back of my mind I was thinking about the 2013 film Enough Said, with James Gandolfini and Julia Louis-Dreyfus.

So, I'm making it my chick-flick recommendation for this weekend's viewing.

Here's why.  I have one big caveat regarding that July 11 blog post:  Like attracts like, and we're cruising for a crash (and a badly bruised ego) when we expect to attract men who are head and tails above the level we're at in our own lives. 

My previous post was about how men's feelings of entitlement are colored by a lifetime of women's petting, coddling, and abetting their shortcomings and bad behavior.  Not to mention daily media photo spreads of the much-younger conquests of middle-aged rich and famous men. 

But can women's expectations be a little off the mark, too?  For sure.

I decided to write about Enough Said because of a couple of recent coaching calls with Dynamic Divorcee clients.

One particular lady in her late 40s, without a decent job, floating while looking for a lifesaver, expressed her goal to find a professional man to support her and her three children so she could stay home and pursue her clothing design hobby.

There's nothing wrong with hoping that a man can help better a woman's financial situation.  Men and women often bring different gifts to the table in a relationship.  So I asked this client to take a look at what she is bringing to the table. What does she have to offer to the mythical Prince Charming?

In Enough Said, Louis-Dreyfus' character Eva, a massage therapist and divorced, single mother, begins dating a regular guy, a self-described "slob" who is actually a person at her own level, and, with this, she immediately begins to find fault.  Should she settle for him?  Should she deserve better?  Intruigued?  Watch and find out what happens.

Back to real life:  What's the best way to meet a great man (and have the greatest amount of choice and power in the relationship)?  Bring to the table exactly what you hope he will bring to you.  Ever notice that the moment you're no longer white-knuckling a situation, you immediately get what you've been longing for?  Same thing here.

Get your financial house in order.  It's way easier to do this yourself than to expect someone else to do it for you.  Show the man you like that you're not expecting him to provide you with the basics.  Let him see that you have your own life, a great circle of friends.  That your life is already full of interests and yummy goodness that you may be willing to share with him, if he's willing to try hard enough to show you that he is the one.

That's an attitude much more likely to meet with success than for a middle-aged woman to expect to find a man willing to do all the up-leveling for her. And, way more fun.  And . . . now you deserve to be picky : ) .

It's summertime again: Forget about dating, and just make new friends : )

When May arrives each year, if there's no one super-special in my life, I can start feeling lonely and disconnected, wanting someone really fun to date for the all-too-short warm-weather months.

So, at about that time, I start paying attention to my online dating site again.  I start taking a look at the available guys, trying to determine which ones aren't quite as old and decrepit as the others, not too deadly dull, and of those, which are not sooo disastrously focused on women much much younger than they.

Heading off the summertime blues
Last year, I wasted the better part of a year going against my own advice -- giving try after try to someone whom I felt was the best of what was available.  And, it wasn't a bad summer.  Fall not so great.  Winter even worse.   

He told me, on one of the first dates, that he had zero emotional intelligence.  I wasn't sure what that meant, but I came to find out. And I was immediately much happier without him. 

When May arrived this year, I, once again, did check in with the dating site, and I did go on a couple of go-see coffee dates.  Meh to the 9s.  (Or, hell to the no!)

I began to consider my motives.  What did I want from this?

Well, shallow as it sounds, I really just wanted to meet someone nice whose eyes sparkled at the sight of me.  I wanted to dine outdoors in balmy weather, and get dressed up for someone who would appreciate it.  I wanted to laugh, drink some wine, share stories both silly and sad.  Go on long walks.  See new things together.  Stuff like that.

It finally occurred to me:  I don't need a man for those things.  I need girlfriends!

This is a job for girlfriends
If you've been reading this blog from the early posts, you know that it started as a 40+ single girl's guide to navigating the weekends solo.  That's because, post-divorce, all of my girlfriends were happily married or in relationships.  They were busy on the weekends, and I would have felt out of place being a third wheel or hanging out with their families.

I had a few things to sort out for myself anyway.  So I spent a couple of somewhat lonely summers
getting comfortable with my own company.

But now, it's different.  And I need to take the same advice that I give my Dynamic Divorcee coaching clients.  It's pretty easy to make new friends and get closer with old ones:  We single ladies just have to make the first move, and make it a few times in a row.

Schedule weeknight dinners for some one-on-one time with girlfriends who are married.  Saturday night out with a couple of lifelong friends who are now single, too.  And sometimes, even a night out with a married couple.

So far, this summer, I've had a lot of fun, and hardly noticed that I'm unattached.  (Well, actually, I'm not completely unattached.  But there's no one in my life right now who has my undivided attention, and certainly no one in town who is anywhere near as much fun as my friends.)

All it takes is a text or a phone call
A couple of my Dynamic Divorcee clients are a little chagrined that it takes so much effort to engineer these social events.  That is, that we are the ones who have to do the calling and occasion-making.  But is that so bad?  How much effort is that, really?

Much less effort than going on boring coffee dates, and even more boring and disappointing second dates, while feeling like maybe you should really try to make this lackluster thing work.  More fun to get dressed up for friends who appreciate it rather than to be looking pretty for a guy who shows up in a t-shirt and shorts.

Yes, for a while, you may have to be the one who calls a certain friend (or someone you would like to have as a friend) over and over.  She's not calling you, and you're the one making the effort.  But, after a few rounds of this, you can ask:  How about you call me next time?

It's good practice to be proactive and go for what you want -- even in friendship.

Give it a try:
1.  Make a short list of some people who make you feel good.  People you'd like to see more of.  These should be people who are upbeat, positive, and encourage you.  People who think you're great.
2.  This week, contact at least three of them.  Suggest a get-together:  Coffee, a drink, lunch, something that doesn't take a huge time-commitment.
3.  Schedule it.
4.  See how you feel after your date. You had fun, didn't you?  Way more fun than responding to messages on OK Cupid.
5.  Repeat.  I have a list of my favorite people in my city whom I may not get to see often.  My goal is to engineer a chance to see each one at least four times a year.
6.  Enlarge your list of friends/potential friends.  Notice when you meet someone in the course of your life whom you'd like to know better.  Then, start with step 2.

Have fun with the rest of the summer!  And let me know how it goes : )

Are men really more attractive as they age?

Is it really true that men become more attractive with age, and that women go straight to the gutter?

Hmm, let's first consider how attractive these older bon vivants are.   We're not talking about movie stars, models, actors, or triathletes.  We're talking about normal, beer-and-whiskey-drinking, couch lounging, self-gratifying 50-ish and 60-ish guys (the ones who are hitting up ladies in their 30s and 40s on dating sites).

Let's consider some of the typical men I see looking for much younger women on my online dating site.  They often look a little like the guy to the left.

If it's not their looks that make them more attractive as they age, then it must be their professional and financial success.  Well, not if I go by the last bunch of cream-of-the-crop dating site men I've recently agreed to meet.

(Full disclosure:  I have a couple of great guys in my life, but I believe in continuing to look until I find the one who really is, in my heart and his, the rest-of-my-life partner.  For me, it's not enough to agree to be exclusive with someone who's not too bad.  Ladies, you know that I believe, utterly, that it's our path to expect more from life, not continue to settle for less.  But, back to the subject . . . .)

Lower Slobbovia
Guys seem to feel no pressure to look attractive (even on the first few dates).  Everyone, no matter how much he's let himself go can clean up for a date.  But many of these guys confuse "being me" and "accepting me for who I am" for not trying.  They feel no imperative to put a best foot forward, but then feel disappointed when a woman doesn't feel like an end-of-date hug or second date (let alone the sex within 3-5 dates that most men are upfront about on OKCupid).

Ladies, if you've been dating post-divorce, you've had some of these dates already.  I'm so tempted to give you little profiles of the guys I've met on recent coffee dates (but I won't):  Every one of them a smart, very-well-educated guy who had consciously lit a match and blown up his life, career, and often his marriage in some creatively obtuse way.  And were pretty proud of it.

Bear with me, I do have a point here.

There's a difference between the ways that men and women are socialized and it really shows up with this "older men still attractive"/"older women the kiss of death" dichotomy.  And hang in there with me, because there's a new insight at the end of this.

We're #2.  We try harder.
Conventional wisdom and popular culture tell women, in every moment of the day, that we should be trying harder, we're not quite good enough yet, our prospects are entirely tied into our looks (not to mention that our middle-aged dates are also concerned with how much money we have).  We're conditioned, from every direction at once, that we should be reducing our expectations and be happy that there's any man our age at all interested in us.

But society hasn't done these clueless old geezers any favors, either.  These poor old gents (actually, I wish they behaved like gents) have been told their whole lives that they are it.  They're used to being served by women, coddled by women, having their egos boosted by women.  The expectations of how we should be serving them (emotionally, practically, sexually) are unspoken and endless.

Show me what you got
This is fueled by all of the images they've spent a lifetime assimilating:  From sit-com moms to the porn that, if my men friends' admissions are any indication, is a bigger part of most men's lives than we ladies would like to know.  Check out the hard-core porn available for free viewing online.  Or check out a lovely magazine like Hustler, to see what kinds of images men are enjoying.

If this is the reality, in their minds, about what they hope to receive from their relationships with us, and many of them are still so upset at how their ex-wives or former girlfriends fell short, it's no wonder that they're waiting for us to prove ourselves to them before they turn on the charm.

Or, they just don't see why they should have to bother at this age.

Okay, here's the insight:  It doesn't have to be this way unless we let it.

Stockholm syndrome
If society tells us an untruth long enough, we start to believe it.  And, we've been hearing this untruth about older men holding their dating-marketplace value (or, even increasing in value) for a very long time.

You've probably already read some research like this, The Case for An Older Woman.  This particular link is all about how guys in their 30s and 40s should open their minds to consider dating someone their own age (or even a little older).  The arguments:  An older woman will be more adventurous in bed; if she's still single, she takes better care of herself and is more attractive than her married counterparts; and other arguments tinged with "and she'll be so grateful."

A woman who believes this stuff may settle for a sub-par guy (or a series of them), and convince herself that this is the best she can do.  It seems a form of Stockholm syndrome -- in which hostages express empathy, sympathy, and have positive feelings toward their captors, sometimes to the point of defending and identifying with them.

If we wake up and smell the coffee, on balance, we can say with certainty that men do not become more attractive with age any more than women usually do.  It's just that we've been told this lie for so long that we've started to believe it.

The ridiculous level of bravado that so many older men exude has everything to do with how men have lived their lives, contrasted against how women have lived.

Self-Love = Power
Because many men have spent a lifetime on gratifying themselves, and therefore increasing their personal power, it's easy for them to grossly overvalue themselves.  No matter how paunchy, flabby, and unattractive a guy is, you may notice that he still has no trouble finding dates.  His self-belief is all that matters. (And, of course, that's bolstered by our society's messages -- and it's a chicken/egg debate as to which came first.)

As women, we've been taught to give our personal power away (defined as being loving, caring, and self-sacrificing) rather than to serve our own best interests, gratify ourselves, and thereby increase our personal attractiveness and magnetism.

So, let's tell ourselves a better story and believe that instead.  Because, if anyone is becoming more attractive with age, it's women who know what they want, surround themselves with loyal and loving friends, create their personal style and surroundings in a way that please them, and make a primary decision-making question, "Will this make me happy?"

The most attractive woman?  It's you, when you decide to be the heroine of your own life story, not just a bit player in your own life.

"Will this make me happy?"
Start acting from your own truth that you are god's gift to men.  Because, if you're a loving, giving, caring woman, you are god's gift to men.  You've been giving for a lifetime already.  You can now be god's gift to men in terms of teaching them how to treat an incredible, irresistible mature woman who is radiating self-love and charisma.

Those who are unworthy of you or unable to appreciate you will fall away immediately, as they should.  And you'll still run into a few mistakes on coffee dates who got past your dating site messaging radar.

But, all it takes to start a revolution in perception is for all of us to make choices from our highest and most beautiful selves, build ourselves up through our every thought, and every book, article, film, and video we choose to consume and start on a total diet of self-love and appreciation.

Want to know exactly how to do that?  I would love to take you through my signature 5-hour virtual VIP Day, "Prepare to Be Loved."  The program prepares you to be loved by another, yes, but more importantly it prepares you to love yourself, which is the key to absolutely everything: excitement, financial freedom, happy relationships, love . . . exactly everything that's important to a happy life.

New Year's Eve with the not-quite-right guy

Here I am on New Year's Eve 2012, on -- what? -- a date.

Although I've meant to write about my experiences with online dating, every time I started a post that veered in that direction, I got so bored that I gave it up by sentence number two.

So, when my long-distance-relationship Mister Wrong of the past five years emerged yet again to darken my door -- and kept coming back during the holidays as a good-faith gesture, I figured that a night out rather than a night at home alone seemed more fun for New Year's Eve.

And it was.

I've found that when it comes to my Mister Wrong, he makes a perfectly fine-for-now companion as long as I keep my boundaries clear, don't let him get physical with me, and keep my head on straight.

I'm fine as long as I don't believe any of his hinted-at-promises (which, at this point, he almost believes himself).  I keep reminding myself something that I've only learned since my divorce:  Yes, some men can retain their trademark teflon properties all the way up to death's door (and perhaps beyond).  Nothing you can possibly do will make more than a passing impression.

No, ladies, don't take the bait that if you only changed about three dozen additional things about yourself that -- aha! -- then, he'll be willing to come through for you.

More from me later on this, no doubt : ) .  But, in the meanwhile, don't take anyone too seriously unless he shows you he's serious.  The right one will have no trouble letting you know.  In the meantime, let's learn from our merry middle-aged bachelor friends -- and have fun.

Something's Gotta Give

I can't imagine that there's any over-40 woman who hasn't seen this film, but it's one of my favorites, and grows on me the older I get.

If you're a single woman of a certain age, you'll recognize the Jack Nicholson character as someone you've encountered on innumerable dates, and from innumerable online dating profiles (you know, the ones where old, paunchy guys photograph themselves on speedboats and next to sports cars).

Absolutely a hilarious film, and worth it just to hear Frances McDormand's gentle rant near the beginning of the picture.  Perfect solo weekend viewing -- reminding yourself why enjoying a weekend pursuing your interests at home can be way more rewarding than that potential coffee date (or, worse, dinner) with that silver, not-so-foxy old fox.