Flirting? Via messaging? ...help?

April 8, 2016 7:11 PM

Well this is new to me: I actually contacted a real-life crush online (!), but have no idea what to do next. Please advise.

I'm female, in my early 30s. Long story short, I ended up finding and contacting a guy I knew in real-life on a dating site (oh god that was scary for me because I had never done that before - I was an anxious wreck beforehand). We had been semi-flirting via eye contact in person for a while now, but we've never spoken until I initiated contact earlier in the week. Anyways, over the last couple of days we've exchanged a few brief messages and he seems to be interested, even asking if I was free this weekend! Unfortunately I already had plans (booo), and he was disappointed (as was I of course).

So yay! Contact! Interest!

The thing is I suddenly remembered how terrible I am at things like this...but I don't have much experience with the whole flirting thing. Especially text/online flirting. I feel like my lack of flirting ability via messaging is somehow going to make him less interested or bored??

- So how to you maintain contact before a proper date without being too...over-eager (even though I'm super pumped) I don't know what a good level of contact I should be having with this person without being annoying or so little that I come across as boring or uninterested. We haven't talked in person and built some sort of rapport yet, so it's rather awkward for me to just start chatting away/ask a bunch of questions right off the bat. I get the impression it's normal out there in adult (over 30) dating world to not have too much contact before a first date, right?

Also, he hasn't asked for my number, but it's ok to give it to him even though he hasn't ask me, right? (cause I really hate the stupid messaging app on the site)

I dunno, I'm pretty sure I'm overthinking this plate of beans with a heaping side of anxiety, but I thought I'd ask you guys for help since I've gotten excellent advice from you all in the past. Thanks!

posted by anonymous to Human Relations (7 answers total)

A nice brief, "How was your weekend?" would be a good way to start, I think. Then he can ask about yours, and you can say, "This might be easier if you had my number," and you're good to go.

Seriously, you don't have to follow any "rules" about how much to chat before your first date. It's not an arranged marriage.
posted by xingcat at 7:18 PM on April 8, 2016 [1 favorite]

Have you nailed down firm plans yet? If you haven't yet, make it happen! It sounds like you're busy this weekend, so some night this week?

After you have the date set, send him your number, "in case he needs to get in touch with you before [x]." At that point, he'll likely either text you or send you his number via the app. Then, outside of acknowledging the receipt of his number, I would wait until the day of the date (or the day before) to confirm over text. I don't think you need to flirt/communicate over text outside of that!
posted by kylej at 7:21 PM on April 8, 2016 [3 favorites]

First things first, absolutely make concrete plans if you haven't yet. kylej has the magic words for the phone number getting.

To answer your question, in a couple days message/text him some random neat thing about your day. It doesn't have to be anything particularly cool, just whatever feels like you that you have an immediate impulse to share, like "I got to pet three different dogs on my walk into work this morning. THREE!" that will break the ice of easy chit chat.
posted by phunniemee at 7:47 PM on April 8, 2016 [1 favorite]

Agree with all of the above. As well as this, I think it can help in a general sense to remember that any situation that is going to go somewhere is unlikely to be derailed by minor stuff and especially not by you being yourself. I recommend not giving too much thought to whether you might be doing too much of this or not enough of that and just trusting that it will work out if it's going to work out.

If you're excited about the process, be excited. I've been on the receiving end of this in a dating context and found it very flattering and endearing. It's nice to know that someone likes you. If he gets weirded out by it then it's an indicator that he wasn't the right sort of person for you to date anyway.

The only caveat on this that there is nothing to be gained from detailing or even mentioning whatever you see as your faults. We all have them and you will each get to know each other's if it gets serious, so there's nothing to be gained from doing it unless there are practical reasons. Be who you are by all means, but put your best foot forward.

Also, the not too much contact before a date thing is more about avoiding getting attached to someone you don't know before you meet them. That wouldn't apply here given that you already know each other.
posted by mewsic at 10:41 PM on April 8, 2016

Just be your sweet, super weird, awkward self. He can't fall in love with you unless he sees who you really are. I know this is scary and really hard (I haven't succeeded with it yet) but, it really is the only way. Do whatever will make you feel more comfortable. Ask him to meet you for coffee one day this week and then progress to phone calls after that. And remember, you aren't trying to convince him of anything or win him over. You are looking for someone who makes you feel good inside. He is filling you up with happy bubbles of joy right now so you are on the right track. And, he is interested, so even if you are the worst flirter in the world, well, maybe that's what he likes about you.
posted by myselfasme at 5:09 AM on April 9, 2016 [1 favorite]

I would keep it light and casual. Don't get into any deep subjects over text before you've actually been on a date, and make plans for your actual date as soon as possible. I like phunniemee's suggestions. And I don't mean that you should act disinterested (if you feel like telling him you're excited about your date, tell him). I've just found that it can be easy to fall into a type of false intimacy over text. I say "false" because in my experience the dynamic usually changes once you're face-to-face, and knowing intimate stuff about someone who is basically a stranger (and having also shared intimate stuff with them) can put you in a sort of awkward place: you still don't really know each other that well, but you both sort of feel like you should be past the small talk stage even though you aren't really, so then what do you talk about? In my experience, anyway.
posted by colfax at 5:32 AM on April 9, 2016 [1 favorite]

I'm just going to say omg yes, just give him your number. Especially if you know him in real life. This is not a thing and just be like "Here's my number." That is a 100% normal no big deal thing. And yes, make a real plan now!
posted by jeweled accumulation at 7:02 AM on April 9, 2016