The Over 40 Dating-to-Courtship 5 Min Speed Test
- Great Aunt Mildred

- Dec 12, 2025
- 6 min read
Updated: Dec 26, 2025
The birds and the bees are mostly a flight of fancy daydream and temporary nostalgic insanity now. This is not new territory. If you’re 40 or above, you likely already have children or don’t want any. There’s really only a few reasons left to humiliate yourself in the dating pool again. Those reasons are generally a sense of security and companionship.
It’s nice to have things your way while living alone.
It’s also nice to have someone visit you in the hospital, laugh at your jokes, and help when there’s car trouble.
This era of hoping to find someone requires a very different catalog of screening processes than your eighteen-year-old hormone-bitten body could dare to demand. But demand you must.
Because the only thing worse than being alone is being alone with someone else who makes you feel alone - or worse.
In light of these things, here are some speed dating questions I think may be worth considering. You can put them in slow mode too; I just like the short form and to-the-point frame of speed dating.
Without further ado:
Vengeful or resentful?
This question cuts straight to the undercurrent of all your future fights. If he/she is vengeful, you will have to one day face the admittance of their intentional betrayal at some point. If they are resentful, well, you may have to endure some uncomfortable silences, overdue emotional eruptions, and cold shoulders. (Personally, I’ll take resentful over vengeful any day because at base level I want to know that my partner/spouse won’t hurt me with cruelty. Been there and won’t endure it again.)
Inside or outside locus of control?
You want this inside. Yes, even if they believe in God (power outside of their control). Those who have an external locus of control view everything as happening to them. They tend to play a victim narrative and a sense of helplessness about everything that happens to them. This is not so great in a relationship because people with this worldview tend to be unable to accept blame or part in any wrong doing in their life. They will rate poorly in accountability in my experience.
Responsible or irresponsible?
Listen, irresponsible is only cute in that song and in fantasy-laden Rom-Coms. I won’t speak for men on this one, but no woman 40+ wants a man-child to clean up after. Women after 40 expect men over 40 to have some sense of maturity. Balance your finances, pick up your dirty laundry, wash your dishes (immediately, not two days later), model some sense of dignity in home life - as much as in work life. A lot of women over 40 have already raised children. They are not looking to adopt an adult version. Boys need not apply.
Video Games or BBQ?
You could also ask Bars or BBQ. If they’re over 40 and still bar hopping… if they’re over 40 and still insist upon video game time… please reference the fine print under point 3 - because he’s not done growing. They say women mature faster than men, but really? Over 40? I’ve learned the hard way that if you have to beg them to break out the BBQ, then you’ll likely also have to beg them to put down their video game long enough to change a diaper. And ok, maybe we’re not in it for kids now, but… these issues are a sure sign of frustrations to come that may or may not be worth it to you.
Is social media a do-or-die hill?
So much of culture has already so lost this battle that only a few of you will even retain the wits to understand this one. First, social media is the breeding ground of infidelity. Whitewash all the talk you want, but your search history, panicked looks, and quick exits speak much louder. Second, have you yet noticed the number of men at any event, in any place, but especially in the bathroom and in their cars, just sitting and staring down at a screen? I have. That’s a big no thanks red flag for me. But some of the women folk aren’t far behind with their snap chat and tik tok brain rot so. This is for you to decide. And to think I’m having to note this for the over 40 crowd! That’s just sad.
‘Just Friends’ with the opposite sex while in a committed relationship?
You should both know where you stand and where the acceptable lines are in a relationship, because this one can cause a lot of future trouble and heartache if not clearly defined and determined ahead of any life-long vows. My opinion? It’s a terrible idea akin to skateboarding down a hill of ice in your skivvies while dragging your partner behind and promising it’s all in good fun. Sure… And no, it’s not normal for him to be taking phone calls from girls he knew in high school at that age. Call it codependent or niceness gone astray but don’t belittle the smarter women with tales about how it’s perfectly innocent or normal. We actually weren’t born yesterday. We don’t swoon because you put on cologne. That was high school. None of us are there now.
Romantic or practical?
While some may only see a centuries long stereotyped debate between the sexes here, pay attention to this is one. This isn’t just the difference between flowers or socks for your anniversary. This may well be the first indication that he’s more into him than he is into you. Men tend to go for the practical things of a relationship but this tendency is predicated upon what they understand and prefer for themselves. Let me put it more simply: If you’ve told him for seventeen years that you want diamond earrings and he continues to give you gifts he thinks you’ll like (and never what you’ve asked for), you’re not just dealing with someone who values practicality. No, you’re dealing with someone who 1) doesn’t listen, 2) doesn’t value your needs or desires, and 3) is lazy. Romance may well be a cover for other deficiencies, but any man with sense enough to care that women value romance will at least answer “Both!” Especially in the companionship of later years, romance is like a full bloom that should be steadied by the soil of practicalities, yes, but enjoyed for its lavish and gentle beauty.
Quality or quantity?
This one reflects some personal preference but is worth knowing. This value will be reflected in shopping habits and purchases, food choices, friendships, and social interactions. A measure of introvert/extrovert preferences may surface here too. Either way, this simple question can provide insight into the ways you will align or disagree.
Peace or passion?
A hot potato. This one can provide the burn or the balm to many relational situations. If they choose passion, watch out for a lack of impulse control, rash outbursts, and a temper. If they choose peace, determine how much fear, apathy, or passive aggression may be mixed up in their idea of peace. You may desire one in bed and the other in social situations, but it’s more likely that the singular choice here will reflect in all modes of his/her life. Even choice of diet could be reflected here. Just something to consider. I think it’s possible to have both but rare.
Dogs or cats?
I’ll admit, this one is more of a tease. But what is it with single men in this age bracket and their dogs? Let me reframe: their dogs they treat like children. I don’t think it’s natural, honestly. It’s off-putting at best. It’s the male version of the proverbial ‘cat lady’… (You know it’s true!) Well, it seems to me that men do act like dogs and women are far more feline - for whatever that’s worth. Either way, dealbreaker or not, it’s best to be prepared for future squabbles. I allow cats on furniture but not dogs. That won’t change. As a counselor once told me, you have to decide what you are and are not willing to live with. And no one can decide it for you.
When you’re young and dumb, you compromise whatever you must to get the girl/guy.
When you’re over 40, that is no longer worth it. There are some things you’ve learned you are not willing to compromise and no amount of sweet talk, manipulation, socks, or flowers can undo that resolve. You’ve suffered in your past relationships.
If female, you’ve likely shaped your entire life around past boyfriends/husbands/suitors wants and wishes and goals. Over 40, you need a grown man who can provide some benefit and aide to your own in-progress life. Not a man child who just wants to tell you how to live it like them, to please them, the way they like it…
Yes, over 40 changes things. Do your due diligence. You’d do no less before purchasing a new fridge. Shouldn’t choosing a companion come with more caution?
Yours Truly,
Great Aunt Mildred




Well said! As a woman over 60, I agree. We’re not looking for a child to take care of. Not looking to be wined and dined with intention of ultimately landing in bed. I find many men are looking for someone to take care of them. I get it, some of these men at my age have cared for a spouse who fell ill unto death and are keenly aware of their own mortality. However, I’ve been a caregiver in my family since I was 9. It is time take care of myself. I The greatest gift my dad gave me was the admonition to take care of me repeated 3 times for emphasis. For myself, I’m good. But…