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Original poster

Thinking trying OLD… what do I need to know?

219 replies

Itisallgoingtobeok · 04/07/2025 13:06

Out of a several decade long marriage for a couple of years and feel like it’s time for me to dip my toe in the water of dating again.

I’ve been mulling over OLD but the horror stories are putting me off a little bit.

So, what do I need to know? I haven’t been on a date since I was 19! All help gratefully received! Safety tips? Dating etiquette? Red flags to look out for, even better green flags to look out for. I’m working on a thicker skin as we speak!

Feel free to talk me down if you think it’s a terrible idea, or egg me on if you think it’s a great idea.

OP posts:
Jasnah · 15/07/2025 06:30

I would avoid generic dates like that, too. I have not met people for a coffee or a dinner date. My worst nightmare would have been just sitting there not knowing what to say. All 3 that I met (and I did meet no.4, too, just as a friend, after no.5 and I hit it off) were on dates where you actively had to do things and were able to observe carefully not only how they interacted with staff, but how they problem solved or what they were like in the wild. Places like laser tag, high ropes, table top game places - they are all much better first dates imo.

And yes, I absolutely second what @Mulledmead said about internet stalking. I found out one guy's exact work title (which was different to the one he'd given me), full name, family details and finally his exact address. It took 30min of social media stalking and a quick look on Google Maps to confirm - and all I had to go on was his Hinge picture, (not uncommon) first name and location.

Lock your social media down and hide your LinkedIn if you're online dating. And always have a wingman, even in a public place. I had a friend primed not only with who I was meeting where, but on standby for an "emergency" call if I needed an excuse to dash, and under full instruction to check in after a few hours. Never needed, but it was peace of mind.

Questions I asked were very revealing, by the way. You drill down into what they are looking for, what attracted them to your profile, ideal first date, best and worst traits, length of last relationship and why they broke up, relationship with their parents, how they spend their weekends. You set a boundary in place like @Itisallgoingtobeok has done and watch carefully how they handle it. You reveal something small but negative about yourself and see how they handle it (any guy who put "no drama" onto their profile also got an automatic no - I don't need someone who is just after an easy life). You gently tease them about something and see what they make of it. You watch whether they show an interest and ask questions, and whether they remember things. You watch the times they respond at (your 5am/ 11pm weekday only crowd are in a relationship, anyone who has time to respond all day every day with lengthy messages doesn't have a job they take seriously), you call or video call before you meet.

My guy almost didn't make it through. He almost failed the info on his last relationship questions because he closed off there, but quickly turned around after I clearly wasn't going to put up with not getting that information. His reaction to my boundary was important. As was the fact he took responsibility for his part in what had happened.

Nt23 · 16/07/2025 06:48

Bloody hell @Jasnah that's more like the plot to a spy thriller than dating. I feel sorry for your 'guy'.

TwistedWonder · 16/07/2025 06:56

Nt23 · 16/07/2025 06:48

Bloody hell @Jasnah that's more like the plot to a spy thriller than dating. I feel sorry for your 'guy'.

Agree. If someone stalked and grilled me like that, I’d be out of there like a flash. It’s a dare not the Spanish Inquisition.

LadyJaneGrey18 · 16/07/2025 06:58

Nt23 · 16/07/2025 06:48

Bloody hell @Jasnah that's more like the plot to a spy thriller than dating. I feel sorry for your 'guy'.

I disagree. I think those are excellent pointers on how to online date, having heard the horror stories of those who haven’t been very very careful.

Original poster
Itisallgoingtobeok · 16/07/2025 07:51

I’ve thrown in the towel and deleted my profile. The whole experience was unsettling. I really didn’t like the number of messages which opened with completely inappropriate questions / comments. Then add the escalation within a few messages to sexual requests, and the abuse when I wouldn’t agree to an immediate handing over of my number has just made me realise that this isn’t for me. I’d rather be single. Maybe Mr Right is out there somewhere and our paths will cross. If not, so be it.

OP posts:
Menopants · 16/07/2025 12:23

It took me a few goes and deleting my account a few times before I settled into it. But yes it is unsettling

Jasnah · 16/07/2025 15:50

Nt23 · 16/07/2025 06:48

Bloody hell @Jasnah that's more like the plot to a spy thriller than dating. I feel sorry for your 'guy'.

My guy feels extremely lucky to have me, and I to have found him. What my grilling and stalking did was keep me safe from predators and figure out exactly who I am compatible with. And while I did not fire all those questions off at once, but weaved them into conversations prior to meeting, if someone cannot handle my very direct approach to things they aren't the person for me anyway.

I came back from one month of online dating with two friendships and a partner who may well turn out to be my "one". Clearly it worked well for me.

Original poster
Itisallgoingtobeok · 09/08/2025 13:46

Well, I decided to have another try. I’ve just been propositioned by a 31 year old. He’s gorgeous, says he likes older women 😂 No strings attached. Got to be a con / bet / laugh right? It’s doing my ego no end of good though!

OP posts:
dontcryformeargentina · 09/08/2025 14:57

Itisallgoingtobeok · 09/08/2025 13:46

Well, I decided to have another try. I’ve just been propositioned by a 31 year old. He’s gorgeous, says he likes older women 😂 No strings attached. Got to be a con / bet / laugh right? It’s doing my ego no end of good though!

Go for it. Older men don’t guarantee you a quality or commitment anyway. If you have to choose between NSA with younger man or NSA with older man - always go for younger - better body / performance.

NowStartingOver · 10/08/2025 12:55

What's the general rule over messaging with OLD? So far all the conversations I've had end up ghosting. Generally seems like one message a day (Hinge is very much your turn then their turn) and then ghosting happens on day 3.

Jasnah · 10/08/2025 18:55

For me, if someone doesn't clearly seem keen, they're out.

My guy messaged me several times on an evening, after work.

TwistedWonder · 10/08/2025 18:59

I think good communication is important so a man who seems low effort from the start is usually showing you how it will be going forward

NowStartingOver · 10/08/2025 19:18

With Hinge it's very much like tennis, your turn, then my turn etc, so I assume you're not going to be bombarded with messages, it tempers it a bit.

Should I really be expecting someone to be from the off to tell me how amazing I am etc?

FenderStrat · 10/08/2025 21:24

Jasnah · 14/07/2025 18:44

So much depends on the dating site you use and how you use them.

I've been pretty ruthless. On Hinge for a month. I discounted anyone who

  • didn't use a full first name (e.g. M or something)
  • didn't bother filling in any profile information
  • didn't bother making their profile remotely interesting
  • put "travelling the world" or anything else on their life goals that would clash with a settled life here
  • didn't have the common sense not to put pictures with their work lanyards/ kids on
  • posted naked or semi-naked pictures
  • posted more than one picture of them holding an alcoholic drink
  • posted pictures at festivals/ all mountain climbing pictures/ anything else I wouldn't want to regularly do
  • posted pictures with women cut out
  • posted pictures where they blurred out faces
  • spoke English with a strong accent (communication is very important to me)
  • is religious enough to post that
  • wants kids
  • has a dog or a great love for dogs (I'm a cat person)
  • liked my image without leaving a comment
If the conversation didn't flow or they didn't respond with 24h, they were also out. Relationships need mutual investment and I didn't want to do all the work. Anyone who hit any red flags was out. Anyone who hit any amber flags without good reason was out.

I whittled the noise down to 5 people in that month, all of whom I gave my number for further Whatsapp and meetup purposes. I made every one of them send me a picture of them I couldn't find online. I asked a series of direct and purposeful questions and watched their reactions carefully before doing that, so I knew we were on the right wavelength before giving them any information.

Two were incompatible in theor chosen/ lived lifestyles; one I wished luck before blocking and removing them, the other got friendzoned. One I met in person, but he clearly only wanted sex, so he got removed. One was fully on my wavelength, a complete nerd, too, but it took 6 weeks until we both found a time to meet up - he lost out to number 5, whom I managed to meet earlier and who turned out to be the man of my dreams.

I never believed the trope that when you meet the right one, you just know. Now I do. But I also know we were lucky to have met when we did; both of us had not been on the site long and we both deleted our profiles within 2 weeks of our first date. So there is a large element of luck, too, because the good ones don't stay on there long.

Any intelligent man with healthy levels of self respect would run a mile.

Jasnah · 10/08/2025 21:32

FenderStrat · 10/08/2025 21:24

Any intelligent man with healthy levels of self respect would run a mile.

Edited
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And yet I bagged a man who has both in spades and is everything mumsnetters on here praise. Within a few weeks of being on there, I might add.

NowStartingOver · 10/08/2025 21:37

It's such a myth to say that the good ones don't stay on there for long.

Bluddyellfire · 10/08/2025 21:46

gravelshuff · 04/07/2025 13:56

I graduated from old dating school with a husband but had several years of expierence after a couple of long relationships in my 20s i was definately out of touch and really had no idea what i was letting myself in for or how hard it would be. I say this as i was 31 at the time, and in a professional career. Took me until i had essentially given up and was 35 when i met someone even remotely decent. I was ghosted, sexually assaulted, abused and got myself into some really dangerous situations (unknowingly at the time but hindsight would have shown redflags in the behaviour) and this was by still being cautious. I met some of the biggest arseholes i had ever met in my life and it changed my perception of the male species.

  1. meet up quickly - no backwards and forwards talking
  2. meet in public
  3. try and work out if they are just looking for sex, this is especially difficult as alot of men who use old are veterans and know what to say and do and can play a long game. Usually they use ‘three date rule’ and will wait that long but not much longer before ghosting whether they get a shag or not
  4. be mindful alot of these guys are married - try to get enough data before meeting up to google them, facebook stalk and instagram. I would go as far at times to look them up on their professional website (yes some were claiming to be doctors - they werent) so you have to be a bit like the csi
  5. if they seem too good to be true they are
  6. ghosting is very common and less to do with you - for example i met a guy locally who was also speaking to girls in the other city next to me - i rightly worked out he was distant with me and dumped him, a couple of months later he was married to a girl from the next city
  7. no one is too busy to not reply to a text quite quickly now adays so if they are waiting until the next day they are married
  8. use your instincts once and for all
  9. set a very high standard for men - a woman told me this on mumsnet and she was so right - so many of them will allow you to float along with them for months to a year whilst you waste your time. Be very intentional and set out your standards straight away, i wanted to be married within a year or two of meeting someone and then start a family. I would tell them that and thankfully the majority of the time wasters knew i wouldnt tolerate their wishy washy ‘lets see where this goes’ and i met my now husband
  10. if you have doubts about their behaviour its worth asking a friend or mumsnet to help as when you have been in a relationship for so long your compass is a bit off - mumsnet was so useful for me during those years ‘give your head a wobble’ was a common phrase

in all honesty i think old damaged me to some degree (you can see this from above rants) - i always knew men were bad but i was sexually assaulted, cohersed into dangerous situations and ended up with a married man twice without knowing it and despite doing my upmost to prevent it. I am not saying this to scare you but just to make you aware its a dangerous place and you have to be very careful. I have now met my husband but still get triggered if i hear or see some of the men i knew from those days. I was also a very independent, career minded woman who owned her own property - there were a few wannabee cocklodgers thrown in there too so if you have anything to lose make sure its ringfenced.

i met a police officer socially and he worked with old woman and some of the stories he told me about woman who had met men on the websites was sobering.

when i met my husband i was cautiously optimistic and as we work in the same career i was able to verify he was indeed single, did work as what be said he was and was able to make sure he was fine - which helped and we were married after a couple of years. He didnt drop the ball once, always arranging another date, was clearly looking for the same things as me. I remember the first night i slept with him having my heart in my mouth the whole next day expecting for the energy to have changrd between us (like the rest of them) and it never changed - i was so relieved.

I met someone whose profile said 'medical' for his career and whose username was something to do with the word doctor. Turned out, he was a health insurance customer service person.

The one who told me about his drink driving convictions (several of) on the first date.

Men saying 5'10" then they're genuinely, measurably shorter than me (5'6").

The one who broke my fingers and I had to phone my dad to come and rescue me at 2.00 a.m.

The one I eventually moved in and bought a house with who after 7 years very VERY nearly had the shirt off my back...

I could go on but I've managed to block most of it out...

FenderStrat · 10/08/2025 22:03

NowStartingOver · 10/08/2025 21:37

It's such a myth to say that the good ones don't stay on there for long.

I think the good ones can often get overlooked in the overwhelming numbers on there. If they are genuinely decent, their profiles are probably gonna be quite realistic about what they're offering and they just might not grab people's attention.

If they do get as far as a second or third date then I think they're genuine worth, might start a show through. But if they don't get a chance in the first place because they're overlooked, they never get to prove that they actually are one of the good ones.

I think it is often true to say that when it comes to internet dating, nice guys finish last.

IDespairOfTheHumanRace · 10/08/2025 22:39

FenderStrat · 10/08/2025 21:24

Any intelligent man with healthy levels of self respect would run a mile.

Edited
Show quote history

Says a man who clearly doesn't like a woman to use her common sense, set boundaries and have standards!

IDespairOfTheHumanRace · 10/08/2025 22:42

FenderStrat · 10/08/2025 22:03

I think the good ones can often get overlooked in the overwhelming numbers on there. If they are genuinely decent, their profiles are probably gonna be quite realistic about what they're offering and they just might not grab people's attention.

If they do get as far as a second or third date then I think they're genuine worth, might start a show through. But if they don't get a chance in the first place because they're overlooked, they never get to prove that they actually are one of the good ones.

I think it is often true to say that when it comes to internet dating, nice guys finish last.

Show quote history

Says a man who is clearly embittered and trotting out the old "nice guys finish last" trope

IDespairOfTheHumanRace · 10/08/2025 22:56

Says a man who is clearly embittered and trotting out the old "nice guys finish last" trope

SpendingTooMuchTimeHere · 11/08/2025 00:03

Itisallgoingtobeok · 09/08/2025 13:46

Well, I decided to have another try. I’ve just been propositioned by a 31 year old. He’s gorgeous, says he likes older women 😂 No strings attached. Got to be a con / bet / laugh right? It’s doing my ego no end of good though!

might not be… nice to have a confidence boost either way.

Firstholiday · 11/08/2025 07:17

@Jasnah I thought your method was great actually. My only concern would be it would literally weed out everyone that I see on dating sites these days!

Jasnah · 11/08/2025 07:56

Firstholiday · 11/08/2025 07:17

@Jasnah I thought your method was great actually. My only concern would be it would literally weed out everyone that I see on dating sites these days!

Thank you. It pretty much did. My extensive list excluded almost everyone. I set my age range to 5 years younger to 10 years older, though, which widened the pool, made sure my own profile was interesting enough to give plenty to respond to, and set aside an hour each morning (and more during the early days when I was on AL) to click through profiles. I'm no standard beauty, either, which meant that a lot of the shallow end of the pool didn't bother contacting me in the first place.

Those who got beyond the original barriers were therefore automatically well-suited to me. In fact, 4 out of the five who eventually got my number responded to a nerd topic I'd mentioned and we spent time discussing that, which meant I was able to see how much thought and effort they put in. All four held the conversation well. The fifth responded to a different shared interest, offering to show me a place that sold lots of what I was interested in - and we just spent our first holiday together travelling to that place and making his chat-up line a reality.

Others who crossed the original barriers didn't make it very far, because they either couldn't cope with my depth, bluntness or intensity. That's fine, we wouldn't have matched in real life, so the conversations died a death. I didn't hold back or try to present myself as anything other than who I am. And as I said, any red flags and I generally unmatched straight away. I never had more than 4 conversations going on that app.

My questioning meant I found out pretty quickly who wouldn't have worked long-term. It just so happened that the second person I met in real life turned out to be the man of my dreams.

NowStartingOver · 11/08/2025 21:40

@Jasnah Seems to have worked for you, but I wonder (particularly for other posters) if after you matched you consider it rude to ask in the first message what their plans are for a relationship and immediate block/ghost if the incorrect response was received?