How do I stop it from being awkward?

[DateNovice]

I’ve been chatting for a while to a friend I used to work with, we’re not in the friend zone anymore and he has asked if I’d like to go out for dinner with him on Saturday.

Although we worked together for 5 years, we were both in relationships the whole time and I only know the colleague chit chat stuff. In a way I feel like I should know a lot more and it’s giving me anxiety over this date as I don’t know what to ask.

We talk about random stuff, day to day life (we both still work in the same field but no longer at the same company) hobbies and have brilliant banter like we have always had, but I don’t want him to think I am treating the date as a joke or friend zoning myself as I can see it potentially going somewhere 😬

This is all new, I have an 8year old and was together with his Dad for 7 of those years and 5 before that, so I’ve not been on a date since I was 19 (so basically what feels like childhood).

I am so out of the loop, I’d go on dates with my exDP but we’d talk real life and the house, mortgage etc, basically every conversation you don’t have on a first date.

I want to spend this time getting to know him, does anyone have any advice on some light hearted or deep thinker questions I can ask? I want to tap in to his personality and adventurous side a bit more.

We’ve spoken about past relationships and we both know some of that anyway as we were colleagues for so long so to be going on a date knowing a bit of someone’s life story is not a usual first date. He doesn’t have any children so those conversations are him asking me questions.

If you’ve made it this far then well done, I’m sure this isn’t a unique situation so I’m looking for advice for that really, how do I date someone I already know

I've just recently started dating again after a 20 year marriage - so I totally know how you feel. As you already know this person, and it sounds like you have at least work interests in common I think you'll probably find once you get started chat will flow.
I'm only new at this myself - but I would say don't go with a pre-prepared list of questions, maybe start by picking up on some small thing you guys have mentioned between yourselves? I guess you must have talked or messaged about this date at the weekend so perhaps he's mentioned something in passing you could comment on?
Just try and enjoy - dating isn't a test and there are no rules or rights and wrong ways to do it. Enjoy!

Ask him what his favourite music is ? Holidays etc

Just don’t talk about work !

Oh wow @iamthrough how are you finding that?

I think I am associating dating with being 19 too much and not having someone new in my 30’s and as a Mum. I really like him and things are going well, we are both on the same page for seeing how things go, but I think it’s because I already know about his life that I just want to find out the small stuff that I don’t know, but I don’t want to just chit chat about shite.

We worked together in a very male dominated workplace so although I have a girly side, at work it was like I was part of the boys banter so trying to stay out of the friend zone. We support rival sports teams do a lot of our banter is about that, but I don’t want to be “laddish” hence wanting a bit of a deeper chat, especially as I have more about me than that, just can’t think what 😂

Also a bit nervous as although we both work in different offices now, if an opportunity came up at either or our original office he would be my senior 🙈

When is the date? Don't worry OP I'm quite sure convo will just flow naturally. You know each other which is already a good basis for jokes and question etc. It will be fine. Pls update

I agree with AddictedToLoveIsland, I think the conversation will flow. Try not to worry about things being awkward.
Why not be up front and say you are nervous, I'm sure he will feel the same! It will break the ice and highlight that you are trying to move on from friend zone territory!
Best of luck, I hope it goes well.

Listening is a really useful skill when you are trying to get to know someone...

Yes, just chill out and respond to the flow of conversation. You are really lucky to know that you already like each other. As flowerarranger says, listening is an underrated skill.

You two have brilliant banter and kept it friendly and professional at work, this sounds like a good indicator that you will both be able to adjust to a dating situation, even if it feels daunting.

Accepting his invitation for the date is a strong indicator to him that you are interested in exploring possibilities beyond the friend zone!

It sounds like you both enjoy the banter and most social interactions (and relationships) begin with light exchange before moving to deeper topics, so you can keep the conversation light until you feel more relaxed and it seems like he is too.
When you feel more relaxed why not be share with him (as you said above) that even though you've known him quite a long time you feel as if you ought to know him better, and there's is a lot you'd like to know about him? This is a lovely genuine compliment and it gives him a chance to say, 'what would you like to know?

The exciting question for you is - what do you want to learn about this person? Where does your curiosity lie? And what do you want to share about yourself? A date is an opportunity to share who YOU are as well as getting to know the other person.

Your feelings in this situation are so understandable as you've not dated since you were 19 and a lot has happened since then. Now is a good time to get to know yourself as you are now. What things and activities do you like? What is important to you? What do you want from life? What topics do you want to talk deeply about? Reflecting on these questions may clarify your thoughts and feelings so you are more easily able to share, as well as listen to his thoughts and feelings. This may help you feel more confident to move into a deeper chat.

One approach is to start with factual questions that you are curious about (eg. Where did you grow up? What was that like?) which can lead to conversation about childhood, families, relationship with family - up to you how deep you want to go. Perhaps there are some things he's mentioned in passing that you'd like to know more about. But if you want to lead with a deeper questions or something more adventurous, and you feel comfortable doing so - go ahead! The key is asking questions that are meaningful to you - ask him about things you are genuinely interested in.

The more real you can be, while also of course being kind and gracious, the more it gives the other person a chance to like the real you. It is also a very attractive quality because it grants others permission to be authentic too.

Thank you for the replies, that is exactly what I needed and wanted to hear. It feels like I’m a teenager again, not in the playing mind games sense, but the adventure. That is what makes me anxious, am I supposed to feel like a teenager? When I was 19 I did, but because I was a teenager! You can see my predicament.

I’ve always appreciated him as a good looking man, he is my type but I’ve never acted on that, told him or wanted to act on that, we were both in relationships. He was more that bloke in the office that if we were single I’d be interested in dating, only now I’ve got the opportunity to explore this I don’t know how to cross that line. Even that is silly as we talk about that sort of thing all the time, just not face to face.

He ticks all the boxes past the dating stage, he isn’t a dickhead, he is very caring and respectful, I know what he is like at work and to work with and the demands in our jobs (this is why both our past relationships have broken down as it’s not a 9-5 and out the door job, we are the ones that have to cancel plans) so it’s a huge positive we are on the same page about that.

My DS would love him, he has older nieces and nephews that we talk about, but I’ve never outright said do you want children of your own and that is a very face to face conversation, but I do want to know. If he says no then I’m the wrong person to date as I have a DS, so I don’t want to find that out too far down the line.

I think I’ll ask him about growing up and what he was like at school and relate that to his work and outside of work personality, but I do want to know some trivial things too. I think that stems from my exDP knowing everything about me and I wouldn’t want him to feel like he knew nothing other than how I take my coffee. I want to know his thoughts on light hearted things like his opinion on marmite, not his opinion on Brexit. Just the stupid shit as well as the deeper things.

What I don’t want to talk work or about our mutual friends that are ex colleagues and then feel like I don’t know him anymore than I did before. Plus how do you go in for the kiss after talking about everyone else you know, it’s weird.

To the PP the date is on Saturday.

Arghhhh why didn’t I just sign up to tinder 😂

Sorry OP but children of his own and being a step parent or a partner if someone who has kids are two totally different things. I don't want children of my own but I dont mind dating someone who has kids.

Oh totally, he will never replace my sons dad, he already has a dad, but if being with someone who has a child isn’t what he is looking for long term then I’d need to know sooner. Likewise if he wanted children, I’m not sure I want any more and would be selfish of me to date him long term if he did. I don’t want to waste anyone’s time.

@datenovice
You clearly have your head screwed on right - fingers crossed for your date

Don't overthink things.
Build on what you have.
You don't need a script. He will be contributing to the conversation too. You will spark off each other.
Just enjoy his company. Park the worries about children, step-parenting etc
for now.
It is ok to tell him.him you are nervous.

You've got this!

When the nerves come up you can think about them as the feeling of excitement, I find it really transforms the feelings. Enjoy the anticipation of the date and that feeling of adventure!

Dying to know how date went OP

@DateNovice how did it go?