The Do’s and Don’ts of Dating for Widowers

Welcome!  You are reading this because after your tremendous loss, you’ve decided there is still life ahead and interesting people to meet. Whether you’ve been out of the dating game for 3 years or 53 years, the scene now is a little different and it’s important to know how to keep yourself safe and avoid opportunists.

It’s not just that everybody does it through their phones and dating apps now.  It’s also that the conversation around consent has changed in ways you need to know about. And also, there are new ways men get targeted by predators – we’ve seen so many people get blackmailed, extorted, and defamed online, and newly widowed men with money are prime targets.

There’s a couple of character types to avoid at all costs (read about them in Nobody’s Victim) but the most dangerous people are the ones who have nothing to lose. People with few ties – no job, no mortgage, no relationships with their kids or family, no money, no long-term friends – are the most likely to go scorched earth on you if you break up or make them mad. We’ve seen scorched earth attacks include: sharing your naked images, sextortion, blackmail, bogus lawsuits, demands for money, false police reports, and smearing your reputation on the internet.


Below is a list of non-negotiable Do’s and Don’ts to keep you safe in this brave new dating world. 


Do avoid desperate people. You need stability right now.  You are recovering from a loss where emotions were high and you were needed as a caretaker. You may unconsciously be drawn toward people who are high drama and needy because being needed is what you’re used to. But lookout for emotional or financial vampires. They’re pretty easy to detect because the drama will start fast and likely involve issues they have with their family, employer, landlord, debtors, health scares.

Do look for people who already have full lives. The most dangerous people are the ones who have nothing to lose. People with few ties – no job, no mortgage, no relationships with their kids or family, no money, no long-term friends – are the most likely to go scorched earth on you if you break up or make them mad. We’ve seen scorched earth attacks include false accusations of sexual assault, sharing your naked images, bogus lawsuits, demands for money, false police reports, smearing your reputation on the internet.  When dating, look for people with full lives and livelihoods – it may feel like there’s no room for you to squeeze in.  But really, it means the other person has intact social networks and won’t depend solely depend on you for happiness.

Don’t flash it. If you display your wealth online, you risk being taken advantage for it.  Serial predators looking to extort via false accusations know a good target when they see one and a rich sad man is like a cash register.  If you date online, don’t post pictures of you on your yacht, flying private, or drinking $2000 whiskey.  Be careful with what information you give away – like where you work, and your full name. Everybody is Google-able. And if an opportunist wants to find out you’re rich (i.e. a lucrative mark), they’ll be able to.

Do keep it public the first few dates. Get to know the person before inviting them home. If a new date is pressuring you hard to go back to your place, consider that a cautionary signal. Sorry, you are not that irresistible. Any normal person is not going to pressure a new widower for sex. Consider that there might be an ulterior motive.

Do get consent.  You need to acquire the consent of a new sexual partner at every stage of sex – starting with holding hands and a kiss.  It may take some time to get used to this, but it can be as easy and romantic as “Can I kiss you?” If the answer is anything other than an enthusiastic “yes” – which can be demonstrated physically or verbally — hold off. At each stage of sex, you should confirm consent and you should do it each time. Consent to kiss is not consent to have sex. Consent to have sex today is not consent to have sex tomorrow. Don’t beg or wear them down. You are not owed sex because you paid for dinner or you’d exchanged flirty texts earlier in the week. A drunk or drugged person can not give meaningful consent and you should not have sex with somebody who is drunk – even if you also are drunk.  This isn’t as complicated or burdensome as you may think. Watch this adorable short video to learn more.

Do play it safe.  You’ve had a vasectomy and she’s post-menopausal so no need for protected sex, right?  Wrong! There has been a consistent upswing in cases of chlamydia, gonorrhea, and syphilis in the United States, and it includes older adults. Among people ages 55 to 64, reports of chlamydia cases nearly doubled between 2012 and 2016. Whatever your age, unprotected sex leaves you at risk for herpes, hepatitis B, HIV and more. So, condoms!  It may have been awhile, but they still sell them at every 7/11, grocery store, pharmacy and bodega.  Never got over the blushing embarrassment? You can buy them online! And the selection will overwhelm you. Oh, and remember to properly dispose so the dog doesn’t swallow by accident.

Do chill out about the sex. Okay, so maybe you’re not as much of a stud as you were when you were last dating and not everything functions quite as well. Go get some Viagra. And also, there are lots of ways to pleasure a partner aside from your member. Check out the toys at and buy some condoms while you’re at it.

Don’t record it without permission. We’ve had cases where our client was recorded having sex without her permission and the offender said it was an ‘insurance policy” in case they were ever falsely accused of sexual assault. In almost all states it’s criminal to record sex without the participant’s permission when they have a reasonable expectation of privacy.

Do keep it private.  Sexting is perhaps new for you. Yep, it’s no longer abnormal to express affection through privately sharing nude images. Make sure the recipient wants them before sending them. Not everybody wants to see the bulge of your Johnson before a first date – remember Anthony Weiner?  If you do send, make sure the recipient is over the age of 18.  And super important, it’s illegal in 46 states to share somebody else’s nude pics with a third party. So, if you are the lucky recipient of somebody else’s sexy pics, don’t show your friends or post online.

Do take it slow.  An unconscious part of you may deeply want company and to be taken care of. Widowers have lost a lot — losing a spouse is the most traumatizing thing imaginable.  You lost your best friend, your lover, your routine. If she suffered an illness, not only did you lose your life partner, but you also lost your role feeling useful as a caretaker.  It’s hard to learn to stop worrying about a sick spouse or to replace all that extra time on your hands you’d spent caring for her. You are likely an emotional mess – even if you think you’re keeping your sh*t together.  Be careful connecting too soon with somebody.  They may ghost because it’s too intense and they can’t live up to your wife’s memory or they may take advantage of your vulnerability (more on that later).  If you get dumped, don’t take it personally or decide nobody will ever love you again.  Dating is all about connection and rejection. You aren’t immune from that.

Do beware of the Insta-wife. Whirlwind relationships don’t usually end well.  Remember, you are vulnerable and yearn for connection even if you don’t think you do.  Sharing emotions and secrets too early is dangerous. It results in us convincing ourselves the other person is trustworthy even if they haven’t yet earned that trust.  That trust is very exploitable. And is how blackmail works.

Do beware of ex-talk. Be cautious around folks who talk badly about their exes or say they’ve had terrible experiences with love their entire life. They may be the common denominator and looking to continue a pattern behavior of unhealthy relationships.

Don’t be a savior.  We know, you couldn’t save your spouse. But that doesn’t mean you should be making up for it by trying to be a hero to all the randoms who pop into your life.  If you have money, it may be tempting to start throwing it around – to pay for a date’s rent or her kids’ car trouble. You might be afraid your money is the only reason people will want to hang out. Keep your money in your pocket and judge people by their interest in your sparkling personality. Folks who become financially dependent on you will often retaliate when you cut off the gravy train.

Do cut-out the crazy.  If somebody seems unhinged, end it. The sooner the better. The more communications and experiences you have with an unstable person, the more attached they become and the more retaliatory it’ll be when you end it. And don’t give them any opportunities to blackmail you or falsely accuse you. That means no sex with unhinged people.

Do avoid the devil you know.  If you have a history with somebody being bad to you, they’ll be bad to you again.  And probably even worse to you now that your wife is gone. Hostile co-worker who suddenly became single? Skip it. Wife’s acquaintance who tried to meddle in your marriage? Nope. And obviously anybody you know is prone to drama or weaponizing the legal system should send off all the alarm bells. Blackmailers will come back if given the opportunity.

Don’t whip it out online. Beware of the attractive woman who slides into your DMs on social media and tries to entice you to strip.  She’s fake and probably not really a woman and likely lives thousands of miles away. Their goal is to seduce you into masturbating on live-stream and is recording you. After you ejaculate, prepare for an email threatening to send the video to everybody you know if you don’t pay up. So keep it zipped online.  In general – and this is true in real life and online – if somebody seems to good to be true, they probably are.

If this has happened to you, more info here.

Do Listen up.  Listen to your friends’ and kids’ thoughts about a significant other. If they express concern, don’t discount that as them being jealous or feeling like you’re replacing your wife too soon.  If you have kids, they want you to be happy. Sure, it will take some time for them to warm up to the idea of you dating, they’re going to be protective of you being exploited or somebody swooping in with bad intentions and an eye for your wallet.  They also love you and have probably dated more recently than you, and are better at smelling something rotten.

The number one rule is to be with people who make you happy! You’ve got new freedoms and there’s no use weighing yourself down with people who are negative or take you for granted. Life is too short for that. The second rule is to date when you’re ready. Society may be judgmental about when you start dating – people may push you into it right away and others might shame you if they think you’re doing it too soon. But don’t take other people’s opinions too personally. They’re probably trying to protect you or are resisting change because of their own sense of loss. Or both. Only you know when you want to dip your toe back in. And it’s okay to try it, and then step out again!

Good luck out there!


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