To pursue or not to pursue? That is the question

[CleverLilViper]

This is my first post here, and I'm really just looking for a spot of advice.
It's quite an awkward post because admittedly, this is stuff that a 30-something woman should have in the bag by now, but I have been out of the dating loop for so long that I'm a little out of my depth when it comes to this stuff.

For a touch of context, I've known this guy since I was in high school. We're now both in our early thirties, and we've remained friends since high school, albeit mainly online friends. It's been a long time since I've seen him in person.

At school, I had feelings for him. It wasn't something that was returned for one reason or another, and so I moved on. Things never got awkward between us. It was what it was. I moved on.

Fast forward a few years, and we're still in contact. Over the years, we've managed to have a few albeit brief conversations over FB but usually, those conversations fizzle out after a day or two. Then we wouldn't speak again for a while after that where the same pattern would arise.

Over the past couple of weeks, things have changed. We're now messaging each other every day, multiple times a day. Often from mid-morning until the early hours. Most of it is just banter, but it's such a difference that I'm curious about him and I want pursue it.

But i'm in a conundrum because I don't want to do anything that may jeopardise a great friendship. If he's not interested in me like that, and I pursue it and have read the signals wrong, it could mean that he would stop talking to me altogether.

Yet, I don't want to potentially miss out on something great (because I really think we'd be great together) just because I was too afraid to try.

So, in your experience, if a guy messages a woman every day, even when he's out with friends, does that indicate some level of interest? I know it's likely that he's just viewing me as another of his friends and I'm barking up the wrong tree (would not be the first time...) but I don't know how to proceed with this one. Or if I even should.

[AramintaLee]

Tricky one. I think it depends on the chat. Is he being flirty? Has he made any sort of hint at meeting up?

Someone gave me some advice a while ago which has actually worked for me and it's "if a guy is interested, he will let you know".

I would probably just keep chatting and see if things build naturally. If you're worried about losing the friendship, just play the long game and see if he makes a move. Good luck!

[CleverLilViper]

Thank you.

He's not necessarily flirty, but he's not not flirty if that makes sense. We've always been the sort to tease each other so it's hard to read if it's just an extension of that or something more.

I think I'm going to do that just keep the conversation going and see where it goes from there. I don't want to steer it too much and end up ruining the friendship. Not that I would make it awkward with him if he didn't feel the same way. Just he might feel awkward if he knew I felt that way and he didn't.

[Gilda152]

With respect it's not a great friendship its a daily text exchange... So I wouldn't worry about jeopardising a thing, just got for it!

[CatAndHisKit]

So who's escalated it from the infrequent messaging to this?

[ulanbatorismynextstop]

It does sound like he's interested, but as pp suggested just wait and see if he makes a move. If he's flirty, you be flirty but no need to put your head above the parapet yet, just let him pursue you.

[bumbleb33s]

Exactly what Gilda said, you’re not going to lose that much.

If it were me I would suggest meeting up in real life, as friends, and seeing where it goes, life‘s too short to just keep dragging this inane chitchat out, also get in before he meets someone else :)

[supercali77]

As a pp said, I found if a man was interested, even the shy ones, they'll make it known.

[Dozer]

Pointless, and a waste of your time messaging loads IMO, unless you/he intend to meet up soon.

Doesn’t sound like it was ever/is a friendship, since you’re interested in more.

[MagMell]

What others have said. It’s a pretty low-grade friendship if it consists entirely of online messages, so you’re not ‘threatening’ anything substantive if you ask him out.

Having said that, while absolutely sometimes friends become romantic partners, it happens when those involved see one another in person and fall for one another — I really don’t see how/why something that is just a matter of messages over decades could suddenly turn into an attraction.

[Pelleas]

Can you suggest meeting up?

If he doesn't want to/makes excuses you can probably assume he isn't romantically interested in you. There's no reason why you shouldn't continue as online friends, though.

If you do meet up, how he is face-to-face should tell you whether he's interested. If he doesn't make a move/suggest another meeting, then he isn't interested.

[Dozer]

Do you live near each other? If so would suggest meeting up: if he’s not interested, it’ll be clear, then cut right back on or stop messaging.

If geography is an issue would just cut back/stop now.

[LemonTT]

If he is interested he will ask you out. There is nothing stopping him, that you know of at least.

You might want to stop being so available. Not as a act of game playing but because you are investing a lot of time and emotion into someone who isn’t really significant in your life. Give that to the people who matter or yourself.

[CleverLilViper]

Thank you everyone for your responses and advice.

We do live near each other. Well not very far at all so it wouldn't be an issue to meet up.

I'm tempted to ask if he wants to go for a drink with me and just see where it goes from there.

[CleverLilViper]

@CatAndHisKit

So who's escalated it from the infrequent messaging to this?

It was kind of him I think but we've both been keeping it going. I don't message him more than he messages me or vice verse. It's quite an equal thing.

[Dozer]

You say ‘we managed to’ about past, infrequent messaging, but it sounds like you would have liked more. If he wanted to ask you out, he could have.

Yes, suggest meeting up and if he doesn’t agree or drags out making firm plans soon, cut right back on or stop contact as it’s a waste of time.

[Techway]

I'm sorry but I think if he was interested he would have suggested a meet up by now.

He might be in a dating void or just enjoy the banter but men don't hang about if they are interested, they want to see you, even more so when there is easy flow of conversation. Sure you can ask him out but doesn't mean he's as keen as you.

What do you know about his previous dating?

[WakingUp55643]

@CleverLilViper I say go for it!!! Sometimes men don't come straight out with it, they test the waters for ages and ages, hoping the woman will make the first move. What if nobody ever made the first move??!!!! Ask him to meet up and see how it goes. I bet he is going through exactly the same in his own mind. I don't think he'd be messaging you into the early hours if he wasn't interested romantically. Do it! Believe me, I've let so much go in my life because of things I've assumed.......so find out, woman!!!! Good luck!

[CleverLilViper]

[quote WakingUp55643]@CleverLilViper I say go for it!!! Sometimes men don't come straight out with it, they test the waters for ages and ages, hoping the woman will make the first move. What if nobody ever made the first move??!!!! Ask him to meet up and see how it goes. I bet he is going through exactly the same in his own mind. I don't think he'd be messaging you into the early hours if he wasn't interested romantically. Do it! Believe me, I've let so much go in my life because of things I've assumed.......so find out, woman!!!! Good luck![/quote]
Thank you. That's what I've wondered if he's thinking the same way as me and maybe waiting for me to make the move.

Or at least give him a signal. I think I am going to see if we can meet up. If he refuses or drags his feet I will have my answer and back off.

thank you all

[yescheese]

I definitely agree with asking him to meet in person and seeing how it goes from there. If you get anything but an enthusiastic 'yes!' and keenness to make arrangements, please read that as a 'not interested' and manage your expectations accordingly, not a 'not yet'. You don't want to get emotionally involved or sucked into wishful thinking if he just wants a texting pal. I say this from experience with a man i used to work with.

[Firefretted]

Best advice I've ever read: if a guy's giving out mixed signals, he might like you a bit but he doesn't like you enough - move on