Help with post-divorce dating for a man in his 50s. Tips? Books? Other?
August 21, 2021 5:48 AM   Subscribe

I'm a 53-year-pld man going through the breakup of my marriage. I'm starting to date again. It's exciting and daunting and confusing! I'm looking to marshal up resources and ideas. Do you have some advice you can share? Something you with you'd known? I'm especially interested in any book(s) you can recommend.

Most of the books I've seen on dating, or even dating-after-a-divorce are for younger people. Most of the books I've seen on "dating in your 50's" are specifically for women. Trying to find some resources that match who I am and where I'm at: 53, cis-man, straight. (Also parent of a little kid, which is its own thing...)
posted by LambSock to Human Relations (24 answers total) 8 users marked this as a favorite
 
The most important piece of advice I can offer is not to date until you have spent some time on your own, and especially not while you are still married. It's hard at first, but if you can find peace with yourself and get to know yourself as a single, autonomous person, you will have a far better chance of being and finding a good partner in a future relationship.
posted by Dolley at 6:28 AM on August 21, 2021 [47 favorites]


Unpacking the piece about being a parent also seems as important as figuring out how to date as someone in his 50s. This will likely be the biggest question for potential dates, more than your age. What kind of parent do you want to be through this process? For me, dating when I had a small child was complex and often challenging. Lots of folks stayed away because of it, and navigating how and when my kid would interact with my dates was a hard process. I read various books more focused on the parenting part than the dating part, none that stood out especially unfortunately.
posted by latkes at 7:48 AM on August 21, 2021


Lots of late 40s / early 50s divorced guys in my circles. Most of the below is learned by negative example, alas:

* Keep your divorce legal stuff to yourself for now, and don't get serious before that stuff is done.

* Decide if you are willing to have more kids. It is the fundamental dividing line in your dating pool.

* Assume women in their 20s and early 30s don't want to date you. If that's of interest to you, they will come to you, or not, and you have to accept.

* Don't try to pretend you're young again but also don't be 53 going on 65; no woman of any age wants either of those things. So do a modest, tasteful shape up of hair, wardrobe, and physique, and emphasize hobbies and fandoms that are neither nostalgic nor grossly age-inappropriate.

* While you will have to use apps, you will also find you are getting dating introductions at a level you never experienced as a younger single guy. The introductions can be overwhelming if you are a conventional good catch (money, not decrepit-looking). You are going to have to be willing to say "no" to introductions that don't suit what you are looking for.
posted by MattD at 7:57 AM on August 21, 2021 [16 favorites]


Wait. Seconding Dolley. Someone who is dating while still technically not-yet-divorced is ... suspect. With your young child in the mix, too, I'd expect all your time to be allocated, even if you don't have custody at the moment.
posted by amtho at 8:13 AM on August 21, 2021 [8 favorites]


Don’t even think about getting into a relationship until you’ve been divorced for at least a year.

According to several of the men I dated, they were shocked at how many women in their fifties were trying to drag them into bed right away. They were all in agreement that these women were to be avoided because they were full of drama.

There tends to be a lot less game playing at this age. If you like her, contact her the next day. Don’t worry about playing hard to get, ain’t nobody got time for that. But don’t be surprised if she contacts you first.

Pretty much everyone is broken by the time they’re in their fifties - physically and mentally. Everyone has some sort of family problem that they have to deal with from time to time. The key is to be aware that you’re broken, and find someone whose broken parts work well with your broken parts.

I had a lot of problems with men who claimed to have “an occasion drink”, who turned out to be full fledged alcoholics. I don’t know if the same is true of women.

Remember how old you are, and remember that 30 year old women are not even a little bit interested in you. You’re a “creepy old grandpa” to them. If they try to insist different, they’re looking for a sugar daddy. Don’t be flattered into thinking they really are just “attracted to older men.”

Honestly, for the most part, dating isn’t that different now if you’re dating people in your age group. You all grew up at the same time with the same expectations about dating.
posted by MexicanYenta at 8:17 AM on August 21, 2021 [10 favorites]


If you try online dating, I considered men only interested in women who couldn’t even be a year older than they were a huge red flag. And it was seriously 95% of all men out there. To me, it said a lot about how they viewed gender in relationships, and what it said was not good.

And yeah, don’t talk about your divorce or complain about your ex-wife and especially don’t complain about child support or being expected to act like a parent. Any woman worth being with will consider commitment to your child a good thing.
posted by FencingGal at 8:27 AM on August 21, 2021 [30 favorites]


There tends to be a lot less game playing at this age.

HAHAHAHOHOHEEHEEHEE
posted by Melismata at 8:30 AM on August 21, 2021 [24 favorites]


I date guys in their 50s. My somewhat personal tips are:
- Figure out your parenting model and responsibilities first. A man who has done that before going on a date with me will get a second date if the chemistry and practicalities match. A man who hasn't done that is a big red flag to me for a lot of reasons. No second dates or one-night stands with those guys for me.
- Get divorced and be on your own for a little while. I no longer date guys in the midst of divorce, not really because there's some legal line in the sand, but because nine times out of 10 it turns out that my role on that date is to be a therapist. It's draining, unfair, exploitative, and most men are oblivious to this habit.
- Figure out what kind of dating and/or relationship you're actually looking for. Dating at our age is very liberating but only if you're able to be honest with yourself and others. It's ok to not be sure, but be honest then about that. I've gone through phases where I only wanted one-night-stands, phases where I wanted FWBs, phases where I wanted a relationship, and phases where I wanted to explore threesomes, same sex dating, dating only younger men, long distance dating, etc. All of these were possible and drama-free because I was clear with potential partners about what I was looking for, and collaborative about figuring out if it was mutually satisfying to continue. Encountering partners who say one thing but turn out to want another, or who aren't honest about what they want, is beyond frustrating. Most women your age have more than enough on their plates and won't want to take this on.
- Be your actual age. I can't count the number of late-40s guys I've gone on dates with who then confess in person that they're in their 50s. If your ego can't handle being your actual age on a dating site, I infer my role in your life will be to stroke your ego and put up with petty lies. It also shows a profound disregard for what women go through.
- Get up to speed on current norms around consent, gender-neutral language, as well as on (peri-)menopause, STDs/testing, and birth control. I for one am ecstatic about these changes in our culture and in my physical being. Encountering a guy who is stuck in the 90s or worse about these issues is not someone I want to befriend.
- Pandemic bonus: if your child will be going between households, if your child is not vaccinated, if your co-parent's household isn't vaccinated, if you have any other health constraints that would cause you to see or not see someone on a date, etc., etc., it can be helpful to articulate those for yourself now rather than try to figure them out in the heat of the moment. This is very similar to conversations about STDs, testing, and birth control - do you behaviors about using a condom, safe sex, etc. that you can articulate now vs. in the heat of the moment.

Some specific recommendations since you asked for books, etc.:
- Try to understand your attachment style with Attached: The new science of adult attachment
- Understand your love language and, even better, be able to understand the preferred "language" of potential partners so you can love them in their own vernacular.
posted by cocoagirl at 9:15 AM on August 21, 2021 [40 favorites]


It has happened more than once that I am halfway through a good first date before I learn that the person I am on the date with is still married (and in a few cases still living with their spouse) and going through a divorce. If you're going to date now, which I don't really recommend for reasons others have already outlined, please put this information in your profile.
posted by twelve cent archie at 9:22 AM on August 21, 2021 [11 favorites]


Late 50s divorced man here who started dating in early 50s. First thing I learned was that while I have baggage, everyone in their 50s has some sort of baggage. Don't judge on a first date. Two, the best dates came from setups from people who knew me. "Hey, a college friend two towns over is divorced/widowed and would be a great person to meet. Do you want her number?" Three, never talk about your ex on the first date. Don't talk about the divorce. Yes, can definitely talk about the kid or kids. Know what it is you are looking for. Marriage, casual relationship, long-term thing, sex, whatever. Know what it is and be clear about it with dates.

I only tried the online thing with one date. I had the benefit (if you view it that way) of being set up regularly by friends. In my town, if you are a normal person ( an NJB so to speak) woman would like to meet you. I also had two rules that were personal to me. One, when my kids were still in HS or coming home on the regular from college, I did not date anyone from my town. Two, my date age range was 7 years younger to 3 years older. I wanted someone of my age/generation. It sucks making reference to something like M*A*S*H and them not knowing what the heck you are talking about.

Always be honest and up front about most anything. "We cannot get together on Wednesdays, I have little Augie here." "Thursdays, I play softball." Whatever.

I do not have a book recommendation. Not sure reading a book at the age of 50+ is suddenly going to turn you into a dating maestro. You are who you are. Think about the reasons for your divorce and the part that is your "fault" work on. Like anything in life, think about what went right or wrong the first time and try to adjust the 2nd time.
posted by AugustWest at 9:31 AM on August 21, 2021 [10 favorites]


Seconding cocoagirl's recommendation about getting up to speed about sex and sexual health (if you're not already up to date).

Some things that still feel like recent changes to me: IUDs are OK now, HPV is a thing, I can buy a vibrator in CVS, some people say "STI" (sexually transmitted infection) as well as "STD", and sexual identities are talked about on a much more varied spectrum than just "gay/straight/bi".

You can use Planned Parenthood's "Learn" page as a starting point.
posted by cadge at 11:00 AM on August 21, 2021 [4 favorites]


* Assume women in their 20s and early 30s don't want to date you. If that's of interest to you, they will come to you, or not, and you have to accept.

Just a point as a women in her mid/late 30s that someone in their 50s pretty much feels too old for me at this point too. Not sure why people think dating someone 15-20 years older than you is suddenly reasonable after a woman passes age 35? Would you be suggesting a man in is mid-late 30s date a woman who is 55?

(Sorry I know this isn't really answering your question and is more responding to the other posters - just felt like it was kind of a weird calculus going on. For what it's worth I did meet a 50-something man recently who seemed interesting and I might have considered dating - but really he seemed too old for me in the end.)

Good luck out there! I wish you happy dating.
posted by knownfossils at 11:33 AM on August 21, 2021 [9 favorites]


Read Come As You Are and The Menopause Manifesto. Also some Captain Awkward columns to refresh up on boundaries and Dr Nerdlove to address any issues about toxic masculinity.
posted by matildaben at 12:51 PM on August 21, 2021 [5 favorites]


I'm here to recommend Singled Out, by Richard Schickel. Unfortunately it's out of print but maybe you can find it used at a reasonable price. I think it has a lot of wise advice for a 50+ divorcé.
posted by JimN2TAW at 2:21 PM on August 21, 2021


You’ve been given such great advice above! I’m in my late 30s & have dated in your demographic. My advice is to be honest with yourself and the people you date. The amount of bullshit & lies I have experienced from older men is tbh actually worse than younger dudes fwiw. I recommend you include a simple line in your profile like “Dad to a great kid! Divorce will be finalized in December 2021.” I am happy to date single parents who are upfront. Seek out feedback from trusted friends of all ages, such as reviewing your profile & even doing practice dates. Therapy is so important and helpful for us all! Consider getting a regular babysitter or two so you can go on dates occasionally: talking too much before a date can often be a letdown for both parties since the in-person vine is always different, even if it’s more positive. If you just want sex or casually date a few people, be straightforward about that. I want a family, in whichever shape or size that may be, so it’s important that I not waste time on people who don’t share my vision. When in doubt, have a second date but as soon as your gut tells you no, politely end things. A great line is “You are cool but I don’t think we’re a good long-term match. I wish you all the best!” You don’t need to necessarily text that after one date if the vibe is blah but definitely don’t ghost if you’ve been out a few times and/or have had sex. Like with anyone, some people won’t want to date you but don’t worry, plenty of people will! It’s less about perfect looks and more about personality, emotional well-being, and physical fitness after age 35 imho.

Be realistic but also don’t settle. I have gone out with nearly 100 people in the past two years and finally met someone amazing!! As we build our relationship. I am SO glad I kept trying: tbh though I feel our meeting was mostly luck or happenstance!! I’ve tried all the apps and have found the men on Bumble to be the best for me. All the apps suck but it’s the go-to in 2021! Bert of luck to you!
posted by smorgasbord at 6:33 PM on August 21, 2021 [3 favorites]


Also, people have discussed safer sex already but here's this based on experience: I know it's hard for most formerly long-term partnered straight men to readjust to using condoms regularly but it's important for your well-being and the well-being of your date/s. If you want to be monogamous with someone, then sure go for it! But if not, please use 'em. Less fun, I know, but definitely worth it. Also, there are great, easy ways to get regularly tested for STIs even without a doctor's appointment: many are free or low-cost and most are more convenient than you'd think!
posted by smorgasbord at 6:40 PM on August 21, 2021 [2 favorites]


Nth-ing the recommendation to be upfront about your divorce status. I don't agree with people who think that by itself is a red flag (my ex and I decided to get divorced in 2016 and due to the cost and required courthouse waiting periods, ended up legally finalizing it almost two years later, but hadn't lived together almost that whole time). However feeling like someone was hiding something about their divorce status would feel very much like a red flag in a person I was otherwise interested in.
posted by augustimagination at 7:12 PM on August 21, 2021 [2 favorites]


I would like to second reading both Cone As You Are and Attached. Super helpful!
posted by sumiami at 9:01 PM on August 21, 2021


If you’re still married and you’re trying to date already, that’s a massive red flag to me. It says you can’t be alone and you haven’t had time to process your last relationship. And how could you, you’re still in it! Dating right now screams looking for a rebound/therapist.

So. Be alone for at least a year after your divorce is finalised and then come back and ask your question. Chances are, it may be sightly different once you’ve had time to get to know yourself and what you want.
posted by Jubey at 2:47 AM on August 22, 2021 [4 favorites]


Other posters' mentions of condoms reminds me to add something about birth control. As a woman done having kids, dating men in their 50s also done having kids, I consider it reasonable to add vasectomy to any conversation about birth control. You may encounter this, too. Yet I've been in committed relationships with two men who didn't want more kids, and the way those men received the inclusion of vasectomy into the conversation was, at best, Neanderthal and at worst degrading of the immeasurable work most women have done being responsible for birth control.

Understand (really: understand) the relentless and compounding experience women from their late 30s onward have had in handling birth control for upwards of two decades of their lives by that time. It is a physical/hormonal, mental, emotional/psychological, administrative, and financial burden of Sisyphean levels. My back-of-the-napkin math shows it to be between $7,000 - $25,000 for 20 year's worth of birth control, if you can get it, and before taking into account the time off from work and the siphoning of other life-minutes to arrange for, manage, acquire, and implement that birth control. Compare that to about $300 for a vasectomy.

Men need to bring a combination of logic, compassion, and shared responsibility to post-childbearing birth control conversations.
posted by cocoagirl at 8:13 AM on August 22, 2021 [13 favorites]


In line with the advice to not date until your divorce is finalized: do not look to date until you have your own place and can invite your dates back to it.

Lots of guys in the midst of divorce want to get out there and date while still literally cohabitating with their soon to be ex wives, or crashing at a friend's place, or in some other temporary and not great living situation. Clearly their logic, if they've thought about it that far, is that they're looking for some woman who'll host dates at her place... thus revealing the immense sense of entitlement that they almost certainly hadn't given a single thought. Inviting a guest into one's home is an act of caretaking. The world is full of dudes who are only too happy to be the recipient of a woman's caretaking and give not a single thought to reciprocating that. In this age cohort most women are wise to this and won't have anything to do with you.
posted by Sublimity at 9:22 AM on August 22, 2021 [8 favorites]


In line with the advice to not date until your divorce is finalized

While I generally agree with this, I do think there are some cases where a divorce is only the last paperwork step of a relationship that had been not-present for a while. Only you know if this is your situation or not. I'm a 50's woman who met my current partner when I was in my late 30s and he was still finalizing some steps in his previous relationship with his son's mother. This is what was useful for me, as guidelines.

- your story about the relationship should match your ex's story. Not that you all need to be friends or even communicating about things other than parenting, but many of us have been on the receiving end of attention from "nearly divorced" people only to find that they weren't nearly as divorced as they implied. If someone you're dating happens to know a friend of your exes, they shouldn't get a totally different story about what's up. This can be tough if you are an on-the-level person to deal with suspicion you may not deserve, but be honest and up front about this. If I went on a date with a guy who was still married and he didn't mention that fact, there would not be a second date.
- your kid should be your #1 priority, and that is what I would want to see from you. Not "Hey sneak in here while the kid is asleep and then out before kid wakes up because I don't want to introduce you yet..." but more "Hey you shouldn't sleep over while the kid is with me because they are my #1 priority" Similarly you and your ex need to have a talk about what dating other people means in terms of having a kid. Some people feel really strongly about this kind of thing, some do not.
- if your breakup was not amicable (for either of you) and you are in a country where it's appropriate, seek therapy. Not so much to process your own feelings but to make sure that anyone you date doesn't need to do this with you and so you know how to boundary whatever communication you have with your ex. My partner's relationship with his ex was... not good, mostly for her-mental-health reasons but things were a lot better once he learned how to have better boundaries around her erratic behavior while they were co-parenting.
posted by jessamyn at 10:45 AM on August 22, 2021 [4 favorites]


According to several of the men I dated, they were shocked at how many women in their fifties were trying to drag them into bed right away. They were all in agreement that these women were to be avoided because they were full of drama.

...

Someone who is dating while still technically not-yet-divorced is ... suspect

My advice when it comes to takes like each of these: Make up your own mind about each of the people you meet. Don't rely on rules of thumb or whatever supposed common knowledge your friends or others might pass along. You're far from the only person who's ever been divorced or long-term separated or whatever other situation you might encounter while dating. Don't be hypocritical and apply a double standard to others who might be going through something similar from a different perspective. Be open-minded, empathetic, and compassionate to people you meet and find out more before you judge them on the basis of their previous relationships where you don't know the full story. They don't know the full story about you yet, either. And your story is still being written; you're not the person now who you may be in a couple years, or who you might be in a different relationship.

But yeah, also, be cautious about who you tell those stories to and at what point. A lot of people, unfortunately, will assume completely ignorant things, like that you're "hung up on your ex," if you so much as mention a past relationship for any reason, even if it's just that you feel a responsibility to inform them. Don't hide it—you have a kid, and that's the reality of your life, so that at least should be in your profile, and it's definitely points in your favor for being forthright about the relationship you have with your kid as a dad—but there's a balance somewhere in there when it comes to telling the rest, and you kind of have to feel people out on when it makes sense to share more. Try to do it early, of course, because you don't want to actually hide anything, but just know that it can hurt a lot to start to connect with someone, build a bit of trust over a couple outings and conversation, then tell them more and see them pull away. Remember that you don't owe anyone stories about your past relationships, but of course it will come up because you have a kid and you're being a responsible adult about that. In reality, hopefully if you're taking time getting things right with the divorce, it's because you're being a responsible adult human who takes into account the needs of others, including your kid, and that's commendable.

It can be useful to have a therapist to discuss feelings like that with as they come up, because as you just start out dating, you're going to feel hurt at various points and what you don't want to do is start to shut down your feelings when that happens. The reality is, you're gonna get hurt from time to time out there.

So keep that in mind. Unfortunately, mention divorce and you do sometimes get judged differently, as some people get suspicious and seem to want to know what was wrong that you couldn't hack it or whatever they might assume might have happened. But unlike in a younger age cohort, people in your age range are more familiar with the reality that sometimes people divorce and sometimes people die and life is for the living. So people may be more understanding than they would be in a younger age group. Nonetheless, try to let judgments roll off if you encounter them; you may get them from well-meaning friends, too. People are in various places with regard to their understanding of how this actually works or how it might work for you; negative, acrimonious depictions of divorce in pop culture really haven't helped. Points in your favor, in my book, if you're upfront when it makes sense to be about what you've learned about yourself, how you've taken steps to create positive change in your life, how you're supporting your kid through this, and where you are on that journey.

Consider overall that people have more options than ever to meet people and live the lives they want to, without unnecessary acrimony and judgment, and that is a blessing. Take each person as they are, not as judgment might cast them in the story you're telling yourself in your head.

And seriously, don't judge dating partners on the basis of whether they would bed you on a first date. Everyone is free to do what they want in that regard, as long as everyone is being safe, and anyone judging that is living by an old, outdated set of rules.
posted by limeonaire at 12:21 PM on August 22, 2021 [2 favorites]


Response by poster: Hi!

Many months later, I am back to this thread. I want to post some thoughts here, based on my experience, for anyone in a similar situation to mine who comes back to read this.

Advice from this thread I’d want to pass on to the next person:

- Yes, be super-honest with everyone you date: About obvious factual stuff like your marital status and your age but also about your intentions in dating. I get the sense that a lot of guys who want to date casually try to hide that fact. That’s shitty to the people who are dating who don’t want that. It doesn't even serve your own selfish needs: if you do want to date casually, be honest about it and you'll find there are lots of people who want that, too.

- Yes, make sure to get up to speed on the latest norms about consent: Things have gotten way better in the past 20 years. Also about STIs and dating etiquette, where I think things have also gotten better. Just in general - communication and clarity are really better than 20+ years ago.

Advice from this thread I wouldn't want to pass on to the next person:

- A few people here said “Don’t date till at least a year after you are divorced”. As a stranger on the internet, I hereby give you permission to date whenever you feel like it. For me, and for many divorced people I’ve talked to, post-divorce dating has been a source of tremendous joy and growth and learning. It might not be for you. Different people are different. It is true that post-divorce is a time of enormous change and intense emotions - so if you are making long-term choices that seem good now, they might not seem good in six months.

- A few people here said some variation of “don’t date women younger than you”, suggesting it is creepy, or impossible, or sexist. As a stranger on the internet, I’d like to give you permission to be attracted to whoever you are attracted to, and to suggest it’s not particularly unusual to find younger women attractive, nor is it terrible to want to date people you find attractive. If you do want to date women younger than you, there may be women who are a lot younger than you who are smart and emotionally intelligent and have their shit together, and happen to be attracted to older men. My experience has been that women like this are not particularly rare. I, a stranger on the Internet, give you permission to date people you find attractive who are attractive to you.

Random extra advice/observations

- It turned out that, for me at least, the question “How to date in your fifties” was easily abbreviated to “How to date”. I found a couple of books on dating. I checked out the Dr Nerdlove blog and podcast (mentioned elsewhere in this thread). That was all *incredibly* helpful.

- My own experience, and yours may differ, is that I was very nervous and worried going into all this, but it has been *amazing*. An incredible time of connection and learning and personal growth and amazing fun.
If you have not been in the dating world for a long time: It is, in my experience, much less sexist that it used to be, much more honest and forthright, and just better in a million ways. The apps make it much easier to find dates than in the old days. If you are worried: It might turn out to be incredibly great, as it has thus far for me.
posted by LambSock at 6:08 PM on February 20, 2022 [1 favorite]


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