Following my divorce a few years back I've been dipping my toe into OLD :-O
So, what would you do if you had matched and with two people on OLD site and they turned out to be best friends, and you had already set a date with one of them when you realised.
I mean in my mind I have nothing to loose by trying turn this into the best possible outcome for me, cos when they find out I'll blow my chances with both of them for sure?
What are your experiences of OLD and how did you turn it into a success?
Best friends of yours or best friends of each other?
If the latter then they probably both know that they are both online dating and it's maybe not surprising that they've both found you to be an option. Ask both of them out on the same date and see how things develop? 😉
How do you know they're friends?
They were both talking about going to the same place on holiday on the same day, with a friend 😀
Sounds like a script for a cheesy romcom! Scribble the details down and Hugh Grant will playing you in the film before long if you play your cards right.
Not necessarily. I reckon plan to go on both dates. They will discuss after the first. If the second cancels you know why.
Bow Chicka wow wow!
My experience with OLD has been that once you're past your mid-thirties, there's a reason that most people are on an online dating site and they're not suitable for a long term relationship.
By definition, the ones that are, don't tend to be on a dating website for long, because they find someone.
I think that they can work if you're in a location and age category where there's an abundance of suitable people to meet and if you're laser focussed on not wasting time on people who aren't suitable.
I believe that the evidence is that they're not a great way of meeting people for stable long term relationships.
As you can tell, I didn't make it work, even though I had plenty of dates, and I no longer do it. I've had more success and more fun meeting people in real life.
Also...

Sounds like a script for a cheesy romcom!
I was thinking more low budget porn, but you do you, as it were.
You're doing better than a friend of my wife, who matched with her controlling ex.
To answer your question OP, I'd put the second on hold whilst you go on a date with the first:
"Hi, you seem nice, but I've got a date arranged with someone else, and it wouldn't seem right for me to be messaging you at the same time."
Then depending on her response, and if the other one didn't work out I'd message number 2 again, but not be surprised if she didn't answer.
Username checks out.
Shag them both. Then get back on the site. Do I have to think of everything round here?
You’re doing better than a friend of my wife, who matched with her controlling ex.
Couldn't she remember what he looked like?
Couldn’t she remember what he looked like?
They matched, she didn’t want to revisit more than that
when they find out I’ll blow my chances with both of them for sure?
Serious answer,
Why? They know you're on a dating site, and therefore dating people, because you... met them on a dating site? You suppose you're the only one getting their dick wet with either of them?
Your worst case scenario here is that you're rubbish and they compare notes.
OK. Perhaps not that serious. But more serious than the previous answer.
MrsMC likes to work with the Great Romance channel on in the background, and I'm pretty sure I've heard this thing work out
Take Cougar along for a double date?
<quote>Why? They know you’re on a dating site, and therefore dating people, because you… met them on a dating site? You suppose you’re the only one getting their dick wet with either of them?</quote>
good that someone with obviously so little experience of online dating can come up with such a “serious” answer 😂
One day I may have to dip my toe in in this world as it were. I have no idea what the etiquette is. somehow it seems simpler just to stay single
I have no idea what the etiquette is.
Go on to Facebook marketplace and search for second hand wedding dresses - gives you a list of newly single women you can sort by size and location.
LOLz
Ha ha, when I first came on here, I presumed, because of their username, that @Cougar would be of the middle aged predatory female on a dating site type…
Sorry to disappoint.
I've gone by "Cougar" for many years, like since the late 80s. The original inspiration was Top Gun. Obviously an alternate meaning has appeared over time, but it's kind of a bit late to change it now. Some folk only know me as that.
Sorry to disappoint.
Slightly sad, but then, as a fellow middle aged man, unfortunately I don't think I'm a target for the other type of cougars any more.
I think I may have a young lady chasing me right now ( I say young - she is mid 40s) trouble is I am so out of touch not having dated for 44 years that I may well be misreading friendliness and I have no idea how to proceed!
I think I may have a young lady chasing me right now ( I say young – she is mid 40s) trouble is I am so out of touch not having dated for 44 years that I may well be misreading friendliness and I have no idea how to proceed!
Is she bringing you pureed foods?
ROFL
I am invited round for food and wine - is that the oldies equivalent of netflix and chill?
Just you and her?
OP puts me in mind of possibly my favourite story, perhaps ever, from a close friend.
Was when we were in college, he and a couple of girls, one who was an on-off GF and the other who fancied the pants off him (he had no idea, and the girls were close friends), had a movie night (oceans 11, as you’re asking). Anyway they are all on a sofa under a blanket and girl A (not GF) decides to make a move and her hand starts to make its way up his leg, gets to the top and starts having a rummage. Our hero is surprised & delighted and lets this continue, but doing nothing. Meanwhile, to his left, GF is having similar thoughts. Her hand starts to make its way up his other leg, gets to the top and joins in, thinking that the other hand is our hero’s. Our hero is not providing any hands here.
Now, at this point what would you do? I’d wager not what happened next…
After congratulating himself in his head and having a big grin on his face he lifts his own, unoccupied hands out of the covers and, whilst pretty much doing jazz hands, proclaims
‘Look! No hands!
Quite why that was what came to mind at that point, I shall never know, the girls were furious with both him and each other, and I suspect he was in very real danger of losing everything that evening! He has since fathered children, the girls had a massive falling out but eventually started speaking to each other and alls well that ends well.
So to the OP, I would avoid movie evenings with the pair of them, or at the very least ones where everyone can see everyone else’s hands.
That's suspiciously close to a David Niven anecdote about him and Errol Flynn sitting either side of an attractive young female member of a minor european artistocratic family at a dinner party.
Unlikely one an 18yo with no appreciation for classic cinema would know/be able to get 2 girls to play along with though?
I don't know. It's a great story though.
I’ve been dipping my toe into OLD
I think I may have a young lady chasing me right now ( I say young – she is mid 40s)
Sounds like she may be looking to dip her toe into OLD too.
I presumed ……@Cougar would be of the middle aged predatory female on a dating site type
he has fake OLD profiles currently stringing along an unsuspecting chap thinking he’s chatting up 2 friends.
It's online dating - nothing's exclusive until clearly discussed and agreed. Most people on there will have multiple options on the go at any given time.
In short, don't worry about it. Go on both separate dates and see what happens.
had a movie night (oceans 11, as you’re asking)
I never watched that, I haven't seen the previous ten.
he has fake OLD profiles currently stringing along an unsuspecting chap thinking he’s chatting up 2 friends.
You should see my Snapchat.
When I reply "well, that's very nice I'm sure, but mine's bigger" then they get angry with me. 🤷♂️
Go on both separate dates and see what happens.
Go on the same date and see what happens.
Have Ocean's 12 on standby.
Haha, provided me with a bit of a laugh this thread did. I did the right thing and avoided a threesome, I mean any awkwardness, by letting one of them down
Good man- keep it simple. Dating looks like a minefield without adding more complications to the mix
I'm a couple of years in with OLD, and it's become a bit of a chore. However, I have met some great people, just so little chemistry.
I do wonder if I have massively high expectations after last dating in my mid 20s and that the same chemical reactions no longer operate in my late 40s.
However, the last few months have been positive as I've met a couple of people that I've genuinely fancied, unfortunately not reciprocated, but it means I'm not quite dead inside....
Last date went well and the second date is lined up for later this week... unfortunately I'm not sure I've matched with any of her friends, yet 😀
In my post divorce days when online dating in my late 30s it was a bit of a fail if I didn't have at least 2 different dates per week. I got so good at the banter and so came across as really confident most dates wanted a second date whereas I'd got addicted to the first date adrenalin rush until I found someone I really liked.
So I'd say date both and others as unless you try all the flavours in the sweet shop how will you now which is your favourite?
