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.