How do I ask people out in an online group?

Question

For the past few months, I've been participating in a group on MeetUp.com. This particular group holds a weekly social event on Zoom and plays online games together every few days. (The issues below, however, apply to all the MeetUp groups I'm in.) Naturally, there are a few women in the group that I'd like to know better.

The trouble is: in the social event, the men always dominate the conversation, and since only one person at a time can speak on Zoom I can't break off and start a smaller conversation bubble. The games nights are no help, either — I've learned the lesson that you can't really befriend people while playing games, because they take all your attention and don't leave you space to converse about anything besides the game.

I'm enough of a regular in this group that I think the people there would see my name and know who I am, but I don't feel like I really know anyone there personally or deeply. Because of that it just doesn't seem right to me to message a girl on Discord and ask her to a one-on-one video call. How can I change that?

Answer 1

I think there's another step you can take, that could eventually lead to having more contact with these women, although it doesn't directly focus on asking them specifically for a one-on-one chat.

My advice would be to treat everyone the same, so even the males that are usually dominating the conversations, and just shoot a message to everyone explaining what you did here: That you're new to the group and that you'd love to chat with them one-on-one because you'd like to get to know them a bit better, and that you feel the big Zoom meetings or game-nights are getting in the way of doing so. You could even drop such a message in a 'group chat' to gauge interest. Inviting everyone can't make anyone feel singled out.

I'm stealing that idea from new co-workers: The team I work on has been working from home for almost a year now, but in that time we've added three new team members and a new product owner. We have a daily 'chattiness' meeting, of about 15 minutes, but that meeting is always dominated by the same person to whine about work from home and her kids. Those co-workers could've singled out the people that don't talk in that meeting a lot, but instead they just invited everyone, including the whiner, for a chat to get to know each other a bit better, if they wanted to.

The second part is important too: Leave a choice (to accept or not). Our team has people that like to keep work and private life separate. Those people are less interested in chats like these and find the 15 minute chat each day generally enough. Leaving the choice up to them gives them a way to gracefully opt-out. In your case, leaving the choice to other people takes into account that some people may just be there for the games and the zoom meetings (those can decline or ignore your invite), while others may actually be looking for the more personal level contact (and they can accept the invite).

With the new team members, we initially planned a 30 minute window to just get to know each other a bit more, talk about our hobbies, where we live, and from there the conversation just followed naturally. With two out of those three new team members, the meeting was too short and at the end, we just planned a next chat to continue talking. We ended up combining these, and chats with already existing team members, into a single meeting, and now every Friday afternoon I hang out with four other co-workers for a little while after work, just chatting about all sorts of things (while not having to listen to whining about work from home and kids).

One last note: A MeetUp that has game nights to me doesn't sound like one where people may join because they're looking 'to get to know people better' based on gender. So it may not be naturally for the women to want to know you better too, not in the way your sentence about getting to know them implies. In other words: While the above tactic might get a few people to respond, it might also fall very flat after that.

Answer 2

I recommend taking small steps first. Something like this

• continue being yourself in these large-group situations. Laugh at people's jokes, say interesting nice things when you're talking, respond to things other people say. You want to be confident that anyone you approach will recognize your name and think warmly about you when they do.
• if there is one particular woman who has more to offer than mere femaleness, you can "court" her in the larger group -- slowly. I have to say that your post doesn't seem to suggest that you see much difference among the women, that simply being female is the only requirement you have, but then again you do say you want to get to know them better, so as you do, you may develop an attraction to one.
• courting techniques vary but taking the time to appreciate her skills (a quick dm of "great move there!" or "phew! thanks for saving me!" or "loved that comeback to Steve's pun!" or whatever makes sense for the game you're playing or the conversation that's happening) with no pressure for anything else is a good first start. As you say, during a game there isn't time for long chats, which is a feature for someone who doesn't know if they want a long chat or not. You say something nice or interesting, they don't have to say much back besides maybe a smiley or a "thank you".
• as a group event - game or social night - winds up, another quick dm that might be seen as the start of a conversation is a low pressure option for her. If you say "wow, great game tonight, how did you learn that / get to that level" or other open-ended question, she can either quickly answer with a fact or perhaps a conversation will start. Ideally, the meeting wraps up and the two of you are dm-ing on discord for 15 or so minutes after, and you both enjoy that.
• if you like the person you're beginning to discover, you can tell her so and suggest you chat again later, separate from the group thing. Maybe she will say no thanks -- in that case leave her be and don't ask again -- but maybe she will say yes please.
• don't start right in with "are you single?" or anything that suggests you're only interested in romance. And don't suggest a one-on-one video call as a first thing. Some time spent in typing will let you truly get to her know better -- and let her know you -- without pressure or a sense of "I'm already obsessed with you even though I haven't even seen a picture of you."
• I hope this doesn't need to be mentioned, but just in case: don't send pictures of anything other than your face unless you are asked, and don't ask for such pictures from her until it's clear there is something sparking and clicking between you.

Women online get a lot of attention, most of it not aimed at who they actually are - their interests, skills, sense of humour, talents, joy -- or even what they actually look like, but just at their womanhood. By taking some time to learn who your group-mates are, and seeing if that actually appeals to you, not only will you increase your chances of finding someone compatible, you will decrease your chances of "scaring off" someone who has probably already received more than her fair share of unwanted attentions. After all, while you're in this group to meet romantic partners, many are not -- and may enjoy a small quiet space where nobody tries to date them or sees them only as a potential romantic partner.

One more addition: please do be honest. I'm not advising you to pretend they made a good move or are good at the game, nor to pretend that you care who they are as a person. I'm suggesting you find a connection based on something you already have in common. This approach may leave you with a few women friends, the kind of people you can ask for advice with dating things later, or it may lead to dating someone from your online group. Both of those are good outcomes. It should also minimize the chance of a woman in your group feeling that she can't be seen as a gamer (or whatever your group thinks of themselves as) but only as someone to date.

I have a public Facebook page, because I am well known around the world in my industry. I use it to promote, say, a conference where I am delivering a keynote, or a new book I have written. Sometimes that page gets messages from men who are all "you have such kind eyes" and "I think we could have something special and beautiful" and so on. It's gross. That page is for my work. To have all that brushed aside by someone who is just looking for a date -- that's really unpleasant. That's where I'm coming from with this advice. Make contact and see what happens; don't just barge up to her and ask for an online date.

Answer 3

If there is someone that interests you, it's definitely reasonable to message them privately however you can do it (e.g. via meetup messaging), and ask them if they'd like to chat privately (what in happier times would be asking them out).

How do I know this? Well, about 7 years ago I was hosting a meetup group. One of the women in the group was interesting. I was 99% sure she wouldn't go out with me but finally decided I might as well message her, have her say "no", and move on.

She said "yes". 7 years down the road, we are very happily married. So it can all work out.

Of course, if the group rules forbid private messaging, don't do this.

Just remember: "You miss 100% of the shots you don't take" (Wayne Gretzky)

Answer 4

Simple. Don't ask them out. Just make friends and go from there. It sounds like you have a discord where you can do more casual mingling that isn't focused on the game, so do that. If there isn't one already, start or ask for an off topic or irl channel or something to enable casual chat outside the games. Women are repeatedly hit on in spaces like this to the point where many don't want to participate at all or retreat to more insular invite only spaces (hi!) so at least I personally earnestly request that you don't use groups like this for dating.

Even if you don't care about my request, you will be more successful with relationships of all kinds in your life in general if you meet people and let your relationship with them fold out in a way that makes sense for what the both of you have going on than to look for someone to fit a specific hole you want filled in your social life.