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How do you ask them??

57 replies

YourFairCyanReader · 20/09/2025 20:24

I'm happily single and not in any rush to meet someone. But every now and again I meet a man, usually in a professional environment, and think it would be nice to date him. In these situations I have absolutely no clue how to approach this. I can chat to him, get on with him, see he has no wedding ring, and maybe get on to the subject of hobbies etc during which he doesn't mention a partner. I can also follow up professionally and add him to my network.

But I'm so scared to say, would you like to go for a drink sometime? In case I've just completely misread the situation. If he said, er thanks but I'm married, I'd be absolutely mortified. Or worse, responded in a way that made it clear the attraction wasn't mutual.

Any advice?

OP posts:
SheSpeaks · 21/09/2025 22:28

I’m open to going on a date. Are you free to go on a date with me?

No worries, always better to ask. I enjoy dates and dating. I’ll let you know how my next one goes. Let’s carry on as normal.

Great. That sounds fun. I’m free a week on Friday.

BlueCupOrangeCup · 21/09/2025 22:32

You don't.

In my experience it rarely ends well.

YourFairCyanReader · 21/09/2025 23:03

BlueCupOrangeCup · 21/09/2025 22:32

You don't.

In my experience it rarely ends well.

Just don't ask out any man,ever?

OP posts:
TheNewWasp · 22/09/2025 00:16

Don't shit on your doorstep, lovely.

YourFairCyanReader · 22/09/2025 06:10

TheNewWasp · 22/09/2025 00:16

Don't shit on your doorstep, lovely.

So if I go to a conference and meet a professional over the coffee break, sounding him out about meeting up again would be sitting on my doorstep? How is that any different to meeting a man in a pub or a park??

OP posts:
Mysticguru · 22/09/2025 06:56

I wonder how many women have spent the weekend on their own because they couldn't bring themselves to smile and say hello to a guy they liked the look of?

They can network professionally but when it comes to romantic connections there's a block.

I'm glad I brought my girls up to be open, sociable and forthright. Yes, they have been burned a few times but at least they're living the life experience. Both have a good circle of devoted friends and are in long term relationships.

PuddyMuddles82 · 22/09/2025 07:07

You go for it. I’d add on social media that way you can find a bit more out about them, what they like, hobbies, family, etc, and then take it from there.

RavenFinch · 22/09/2025 07:08

YourFairCyanReader · 22/09/2025 06:10

So if I go to a conference and meet a professional over the coffee break, sounding him out about meeting up again would be sitting on my doorstep? How is that any different to meeting a man in a pub or a park??

If you do the asking and make the moves on a man you neet at a conference, he will think you are cheap and easy. You may well end up with lots of meaningless one night stands at different conferences - if that's what you want.

Men are wired to chase. **

** and when women come on too strong / do the chasing / do the asking ...... you upset the apple cart, the wheels fall off and men won't do what they are biologically programmed to do (to hunt, pursue and chase their mate).

Whilst it is the 21st century, unfortunately we need to acknowledge biology and how men are wired.

So in the 21st century as a modern independent woman meeting men at work / conferences, you can be:
● sexy, confident, flirty
● intelligent, radiant, interesting
● have loads of things to chat about
● able to talk about your wonderful job / your wonderful life

But don't pursue.

Let these conversations happen naturally and let the man take the lead.

Don't ask a man out
^^ It is unlikely to end well. (I have done it and speak from experience.)

Read either of these dating books:
● The Rules
● Steve Harvey - How to Act Like A Lady But Think Like A Man

RavenFinch · 22/09/2025 07:14

BlueCupOrangeCup · 21/09/2025 22:32

You don't.

In my experience it rarely ends well.

This !!!!

I have asked men out directly twice and been turned down - it is a horrible feeling.

I've also occasionally come on too strong with a man - it names them back off and run for the hills. **

* On one occasion quite recently a man who had* been flirting with me and seemed to be building up a flirty friendship with me which appeared to be mutual. However, when I pushed it slightly too far, he backed off and I realised he had only been humouring me with the previous flirting - he found it amusing and liked the attention.

Leave it to men to ask for dates / make the big moves / take things to the next level.

You continue to be witty, scintillating attractive company and friendly in their company -- and one of them will make it clear to you when he wants to make a move / actively pursue you.

Gymbunny2025 · 22/09/2025 07:22

At a conference I would just see it as making connections and friends. Realistically the vast majority won’t be single anyway. I would practice asking lots of people you meet and like (not just the ones you fancy) if you can add to instagram (or whatever). You then have time and opportunity to see if they are interested, married, where they live etc.

xSideshowAuntSallyXx · 22/09/2025 07:37

"Fancy going for coffee/a drink after work/the gym".

It's that simple. I've done it many times, not all of them have said yes, some have said "sorry, I can't". You then pick yourself up, dust yourself off and go about your life.

A decent man is polite enough to say no without making a big deal out of it. Jeez I asked one guy out, he said no, next time I saw him he was his usual self with me and we carried on as normal.

You don't turn into some cheap, one night stand because you've asked a man out. It doesn't make you some weird crazy woman.

It's 2025 not 1845.

PensionMention · 22/09/2025 07:46

After further study I met all my boyfriends through work. First was at a conference, next was through a friend who was in another dept and the third and now DH for many years who was a colleague in my dept.

First was just a mutual immediate attraction, lasted a year was fun but not lasting second was me just not seeing a lifetime together though lasted close to 2 years. DH was a friend for a year before we dated. It is a risk dating at work.

Foundationns · 22/09/2025 07:53

TheNewWasp · 22/09/2025 00:16

Don't shit on your doorstep, lovely.

It’s not. There is unlikely to be a work complication. If you fancy someone and feel it’s mutual, you could say :I’ve enjoyed our chat. Want to meet for a drink sometime?
Of course many attractive men are in a relationship already so be ready for that possibility. But I would not ask until you’re actually on the date.

Thatsthebottomline · 22/09/2025 08:23

Let these conversations happen naturally and let the man take the lead.

What a lot of bollards. It's not the 60"s.

Gymbunny2025 · 22/09/2025 08:28

Foundationns · 22/09/2025 07:53

It’s not. There is unlikely to be a work complication. If you fancy someone and feel it’s mutual, you could say :I’ve enjoyed our chat. Want to meet for a drink sometime?
Of course many attractive men are in a relationship already so be ready for that possibility. But I would not ask until you’re actually on the date.

You wouldn’t ask if they were single until you were on a date with them? That’s the complete opposite of how I’d feel!! I wouldn’t even want to ask unless I knew they were single

Foundationns · 22/09/2025 10:54

Gymbunny2025 · 22/09/2025 08:28

You wouldn’t ask if they were single until you were on a date with them? That’s the complete opposite of how I’d feel!! I wouldn’t even want to ask unless I knew they were single

The date would be a coffee or a drink. I’d ask a man for that because I was interested in him but not wanting to spell it out. If he said during the date that he was attached or I suspected he was, I would leave it there.

Mysticguru · 22/09/2025 11:59

Men might have been hard wired to chase but not anymore. The male is evolving. They're not neanthederals nowadays. They're sensitive and rejection by women is just as hurtful as women being rejected by men.
Just look at the declining birth rate across the globe. Especially in Japan. These non chasing men are labelled herbivores and far out weigh the female chasing variety.
Maintain old fashioned perceptions if you wish but it won't get you far in either business or romance.

YourFairCyanReader · 22/09/2025 17:09

I'm really surprised at how many of you think I should wait for the man to make the move. I honestly have been thinking for some time now that a professional man in his 40s-50s, faced with a similar professional woman who is independent, confident etc, would be really unlikely to do this without strong encouragement. There's so much that can go wrong for him in terms of causing offence and misunderstanding the situation. Also I think they are a bit blind to signals, no?

About half of you have encouraged me so I think I will message the chap on social media and say it was nice to meet him and to give me a shout if he fancies a coffee sometime. I am fairly sure he is single and we have spoken on a number of occasions.

But maybe this will tell him I am loose and easy!!! Ha!

OP posts:
Gymbunny2025 · 22/09/2025 17:30

YourFairCyanReader · 22/09/2025 17:09

I'm really surprised at how many of you think I should wait for the man to make the move. I honestly have been thinking for some time now that a professional man in his 40s-50s, faced with a similar professional woman who is independent, confident etc, would be really unlikely to do this without strong encouragement. There's so much that can go wrong for him in terms of causing offence and misunderstanding the situation. Also I think they are a bit blind to signals, no?

About half of you have encouraged me so I think I will message the chap on social media and say it was nice to meet him and to give me a shout if he fancies a coffee sometime. I am fairly sure he is single and we have spoken on a number of occasions.

But maybe this will tell him I am loose and easy!!! Ha!

I think that is a perfect message to send. Good luck!

Crushed23 · 23/09/2025 14:37

Be careful of men ‘failing’ to mention a wife / girlfriend.

I have only ever properly asked a guy out once and it turned out he had a fiancée. He just didn’t think to mention her in our chats (which spanned a few weeks).

Thatsthebottomline · 23/09/2025 14:43

Maybe it'll say to him that your the kind of woman that if she sees something she wants, she goes for it ? That life's too short to wait around thinking "What if"?

Surely thats a very positive image?

Gymbunny2025 · 23/09/2025 15:15

Crushed23 · 23/09/2025 14:37

Be careful of men ‘failing’ to mention a wife / girlfriend.

I have only ever properly asked a guy out once and it turned out he had a fiancée. He just didn’t think to mention her in our chats (which spanned a few weeks).

💯 this. I would assume successful attractive men in their 40s and 50s are not single until proven otherwise. They will however enjoy the ego boost and maybe even consider you as a potential OW.

YourFairCyanReader · 23/09/2025 15:20

Crashed and burned, ladies!!

Received a very nice message back which politely indicated he would not be taking me up on the coffee.

But, do you know what, I don't regret sending the message. I've hopefully given him a little ego boost, I've proved to myself I'm not afraid to do it, and I'm not going to give another thought to why it was a no, because it could be for any reason at all. And I only met him briefly anyway.

Next!!

OP posts:
Thatsthebottomline · 23/09/2025 18:36

Gymbunny2025 · 23/09/2025 15:15

💯 this. I would assume successful attractive men in their 40s and 50s are not single until proven otherwise. They will however enjoy the ego boost and maybe even consider you as a potential OW.

That depends on your definition of "successful and attractive".

StarlightLady · 24/09/2025 07:34

YourFairCyanReader · 20/09/2025 21:40

Really? Do you not think men are more likely to wait for a woman to make the first move, be worried about causing offence and so on? Bearing in mind this is at professional networking events, on courses, at conferences etc.

I don’t think men are more likely to make the first move and don’t see why they should. In fact l’ve had someone say to me in the past that l was the first woman to ask them.

l’ve asked men in the past. Whether it’s a man or a woman doing the asking both could be misconstrued. But you don’t get anywhere in life without taking a risk or a gamble (not financial gamble).

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