How do I ask out someone I barely know and don't see often?

[Pianooooooss]

Let me explain.

I run this little social-justicey event space and there's a guy who's been showing up to our events for the past 6 months now. He was just a cute acquaintance to me, until he flirted with me a bit at this movie event we inadvertently showed up at together, and now I want to get to know him more. 

Thing is, I've only seen him around at the pace of 1-2x/month, and things are slowing down at our event space, so if I just wait around, it's likely I won't see him for a long time. I'm trying to be more proactive in my dating life, and I just realized I have his contact on Signal and I could hit him up.

But...I don't know *** to say or do. I only have his Signal contact because our book club group chat is on there. DM'ing and inviting him to a date 1:1 seems premature and too straight-for-the-gusto. There's also the thing of us being mere acquaintances that've only seen each other 1-2x/month...how do I not make this seem stalkerish or too forward?

Help!

TL;DR I want to get to know this guy more, but I don't see him often enough to wait on another IRL chance meeting. How do I DM him out of the blue to non-suspiciously initiate more 1:1 time?

[SooSad33]

Why don't you just send him a DM and have a bit of a chat first?

Then consider mentioning maybe another 'movie'.. just the 2 of you - or meet up for a coffee?

You hafta get to know him more one way or another.  You really don't even know IF he is already involved or anything.

Maybe a coffee meet, you will learn a little more of these things, then go from there.. ( make note: If he admits he is freshly out of a relationship or marriage, don't even thin twice- walk away.. lol ).  Believe me, you don't want to be a rebound 😉 .

[Pianooooooss]

23 minutes ago, SooSad33 said:

Why don't you just send him a DM and have a bit of a chat first?

Then consider mentioning maybe another 'movie'.. just the 2 of you - or meet up for a coffee?

You hafta get to know him more one way or another.  You really don't even know IF he is already involved or anything.

Maybe a coffee meet, you will learn a little more of these things, then go from there.. ( make note: If he admits he is freshly out of a relationship or marriage, don't even thin twice- walk away.. lol ).  Believe me, you don't want to be a rebound 😉 .

Eeek!

There is something he mentioned at the movie -- a local org or something -- that sounded interesting and I need him to remind me the name of. Maybe I'll just ask about it and it snowballs into a conversation.

[Mason Parsons]

Keep it casual, like asking if he's up for grabbing coffee or something. Mention the book club or the events as a segue to why you thought of hitting him up.

[Pianooooooss]

23 minutes ago, Mason Parsons said:

Keep it casual, like asking if he's up for grabbing coffee or something. Mention the book club or the events as a segue to why you thought of hitting him up.

Oh, man! This is really bold. You gotta give me a script I can use. 😅

[Batya33]

3 hours ago, Pianooooooss said:

Oh, man! This is really bold. You gotta give me a script I can use. 😅

I don't think it's bold - you simply are asking someone out for a date.  I did so a number of times -not bold -no real biggie. I didn't do it often for other reasons - but sure mention a common interest or convo you had and segue. Happens all the time.

[TeeDee]

I agree DMing him to talk about the book or follow up with the organization he mentioned.  

A technique I liked to use to gauge a man's interest was to mention somewhere I planned to be to see if he showed up.  If you can find a related event, say to him that you will be attending.  See if he asks more Qs or if you can casually suggest he attend too.    Since you run an organization find a reason to have another event & invite him. 

[Pianooooooss]

7 hours ago, Mason Parsons said:

Keep it casual...

 

1 hour ago, TeeDee said:

I agree DMing him to talk about the book or follow up with the organization he mentioned.  

 

3 hours ago, Batya33 said:

I don't think it's bold - you simply are asking someone out for a date. 

Okay...so, I did it.

I just asked him what was the name of the organization and he came back right away with some names. He sounded friendly, but nothing that sounds like interest.

I don't think he's out of my league or anything, but I'm really trying to reframe this in my mind as us both being on equal ground and me simply making the first move vs me feeling like a stalker hanger-on. 😕

How TF do I move the conversation forward now?

[Wiseman2]

10 minutes ago, Pianooooooss said:

I just asked him what was the name of the organization and he came back right away with some names. He sounded friendly, but nothing that sounds like interest..How TF do I move the conversation forward now?

That's a good start. Perhaps invite him to something. Drinks coffee lunch? 

[Pianooooooss]

12 minutes ago, Wiseman2 said:

That's a good start. Perhaps invite him to something. Drinks coffee lunch? 

Maybe a, "Thanks! Also, if you ever know another cool movie event or likewise, I'd love to go again!" Or is that too passive?

I tried to find a cool local event to go to invite him to, but none looked interesting. 

Isn't it weird to go straight from talking about org recommendations to asking out someone for lunch? Yall gotta give me the words to say 😂😭

[smackie9]

3 minutes ago, Pianooooooss said:

Maybe a, "Thanks! Also, if you ever know another cool movie event or likewise, I'd love to go again!" Or is that too passive?

I tried to find a cool local event to go to invite him to, but none looked interesting. 

Isn't it weird to go straight from talking about org recommendations to asking out someone for lunch? Yall gotta give me the words to say 😂😭

Why not invite him to an event of some kind. Say like: Hey there's this______ happening next week want to check it out with me? 

[Pianooooooss]

25 minutes ago, smackie9 said:

Why not invite him to an event of some kind. Say like: Hey there's this______ happening next week want to check it out with me? 

The only thing I can think of is a big art collective event we're having our event space tomorrow! But I'll be busy the whole day and it's not a 1:1 date thing. 😕

Wait -- maybe I can invite him to hang out after it ends at 6pm? Like, "Hey, are you coming out to our art event tomorrow? I'm going to be busy most of the day, but...." 

And then I don't know how to finish that sentence. 😂

[Andrina]

but afterward plan to chill and check out this (bar, cafe, restaurant) I heard is good. You interested in joining?

[Batya33]

2 hours ago, Pianooooooss said:

 

 

Okay...so, I did it.

I just asked him what was the name of the organization and he came back right away with some names. He sounded friendly, but nothing that sounds like interest.

I don't think he's out of my league or anything, but I'm really trying to reframe this in my mind as us both being on equal ground and me simply making the first move vs me feeling like a stalker hanger-on. 😕

How TF do I move the conversation forward now?

Suggest a phone call -he didn't "sound" anything -this is words on a screen.

[Batya33]

2 hours ago, Pianooooooss said:

Maybe a, "Thanks! Also, if you ever know another cool movie event or likewise, I'd love to go again!" Or is that too passive?

I tried to find a cool local event to go to invite him to, but none looked interesting. 

Isn't it weird to go straight from talking about org recommendations to asking out someone for lunch? Yall gotta give me the words to say 😂😭

I worked with my husband and we met at 3 work events -same company, different departments and floors - after the 3rd event - over a period of 8 months- with no context at all he called me at work and asked me to have lunch.  We spoke one other time on his first day of work - no other contact.That simple.

[Pianooooooss]

20 minutes ago, Batya33 said:

I worked with my husband and we met at 3 work events -same company, different departments and floors - after the 3rd event - over a period of 8 months- with no context at all he called me at work and asked me to have lunch.  We spoke one other time on his first day of work - no other contact.That simple.

Thanks for the encouragement. Because I posted this on another forum and people are calling me obsessed and desperate.

The only reason I feel the need to do this is what I said in the OP and that I'm on the clock during the event tomorrow (I'm tabling for an org) so I literally can't leave until the end. If he shows up at 11, leaves at 12, but I gotta stay there till 6, it's a bust.

So, yeah. This is what I'm going to say. "Hey, are you coming out to our art event tomorrow? I'm going to be busy most of the day, but afterward I'm going to chill and check out this restaurant I heard is good. You interested in joining?" And totally leave the ball in his court then.

[Wiseman2]

2 hours ago, Pianooooooss said:

 -- maybe I can invite him to hang out after it ends at 6pm? Like, "Hey, are you coming out to our art event tomorrow? I'm going to be busy most of the day, but...." 

It's ok to be polite.  Just ask if he's attending the event and suggest doing something afterward. Leave out the  busy remark. It adds nothing to the text but confusion. 

[Pianooooooss]

5 minutes ago, Wiseman2 said:

It's ok to be polite.  Just ask if he's attending the event and suggest doing something afterward. Leave out the  busy remark. It adds nothing to the text but confusion. 

So: "Hey, are you coming out to our art event tomorrow? I'm going to be tabling for [org name here], but afterward I'm going to chill and check out this restaurant I heard is good. You interested in joining?"

[Wiseman2]

1 minute ago, Pianooooooss said:

So: "Hey, are you coming out to our art event tomorrow? I'm going to be tabling for [org name here], but afterward I'm going to chill and check out this restaurant I heard is good. You interested in joining?"

It's still a bit oblique and confusing as if you're trying to sound overcasual rather than interested but it's better than saying you're too busy. 

[Pianooooooss]

2 minutes ago, Wiseman2 said:

It's still a bit oblique and confusing as if you're trying to sound overcasual rather than interested but it's better than saying you're too busy. 

I'm getting so much conflicting advice. Some people are like, "Ask him out very directly!" and others are like, "OMG, he's not interested, you're going to get played." 😕

[smackie9]

Just suggest going for a quick slice of pizza afterwards and hang out. That's it. Keep it simple. Don't over think it. 

[Wiseman2]

7 minutes ago, Pianooooooss said:

 others are like, "OMG, he's not interested, you're going to get played." 😕

But your nebulous approach won't help that.  You're not going to get played. That's ridiculous. The worst that could happen is he's busy or not interested. 

[Pianooooooss]

Welp. I sent it. 🤪

[Andrina]

It's usually better to take a risk than not try at all. If it doesn't pan out, you at minimum gave him an ego boost and most importantly, you can emotionally move on. If it works out, your life could take on a wonderfully new direction.

[boltnrun]

And don't feel like you have to cringe or hide from him or stop going to the events if he politely says no. I've been turned down and I just kept attending the events I met the guys at. It was fine.