Online dating: how long before asking him out?

[redips]

Hey guys.

So last year, I got out of a long relationship. After gathering myself a bit, I joined some gay social groups, tried to expand my social circle, this and that. Over the holidays, the loneliness kinda got to me, so I created a profile on OKCupid and thought I'd try online dating again.

The thing is: I haven't done this in 6+ years, and the last time I tried, I remembered I wasn't quite good at it. I don't remember getting a single, real-person date out of it. My troubles resonate with what others have said plenty of times: many guys don't respond, and those who do, eventually drop off.

The thing is: I'm really bad in gauging interest. There are guys who would write me long, thoughtful messages; I'd think they were interested, and just then, they'd drop off without saying a word.

So I googled this (of course) to see what (if anything) I might be doing wrong in the past. It turns out that maybe I stayed in the emailing/messaging phase for way too long. I'd always thought that we'd chat for a couple of weeks, then maybe meet up for coffee or dinner.

The thing is, I didn't want to seem pushy and/or desperate. I'm also pretty shy, and probably afraid of rejection. So I've always waited, partly hoping for the other guy to ask me out. I've always waited, even though I would have no problem meeting a guy after one or two messages, or a day or two. (Hell, I'd even meet him right away if he's hot.)

So what do you guys think? If I'm interested in him, how long, or how many messages should we trade, before talking on the phone, or setting up a real date?

2-3 emails?
5-10 emails?
2 days?
1 week?
2 weeks?

What's the verdict?

 

[AstareGod]

I don't think there's any black or white rule to this. I think it's up to the individual people as far as how much time they would need between meeting online and meeting in person.

If I were a person you contacted and I wasn't ready to meet in person, I'd simply let you know I wanted to exchange a few more messages and get to know you more first. If things continued to go well, I'd definitely meet up. Seeing someone demonstrate that they are capable of respecting another's feelings and comfort zone can be very positive.

The time I would wait may also change depending on my mood and what I have planned during the next few days. I tend to be spontaneous, so if someone were to message me one day, I may even be up for meeting them that night, or I might want to wait a few days or even a couple weeks. Keep that in mind with the guys you message.

That said, if you feel the time is right to meet them, why hesitate? Go ahead and ask him out! If he's not ready but can't simply be mature and tell you he's not ready and instead runs away, do you really want someone like that in your life?

Some guys may also like interacting with others behind a screen and keyboard without necessarily wanting to take it further. That can be frustrating, but unfortunately it comes with the territory.

The best you can do is keep trying. Good luck!

 

[HunterM]

Here's the problem. "So I've always waited, partly hoping for the other guy to ask me out. I've always waited..."

Don't wait for people to ask you out. Step up and take charge. If you feel there's a connection/attraction, ask him out. When you get hungry, you don't wait for other people to feed you, right?

Step up and take charge on asking him out. DON'T write, "Would you like to go on a date?" Be assertive. DO write, "Would love to get to know you more, handsome Let's meet up for a drink (or coffee) this weekend...my treat. Will you be free this Saturday?" Flirt with him by calling him "handsome ". Take charge in setting up the date. Telling him "my treat" to show you are generous and to let him know he just needs to show up. Who does not like free stuff?

If he messages back that he's not available...then be persistent, "How about Sunday afternoon?" If he turns you down three times or more, then drop him like a hot potato. Move on to the next one.

 

[darden]

back in my online dating days, my rule was about a week before I'd ask them to meet up IRL. if they were cagey or kept on rescheduling, I'd assume they just weren't that interested and drop them.

of course, I also stated it outright in my profile... "why waste weeks of texting only to discover there's no chemistry 5 minutes into a first date? anyone want to grab a drink after work?"

 

[Disturbance]

back in my online dating days, my rule was about a week before I'd ask them to meet up IRL. if they were cagey or kept on rescheduling, I'd assume they just weren't that interested and drop them.

of course, I also stated it outright in my profile... "why waste weeks of texting only to discover there's no chemistry 5 minutes into a first date? anyone want to grab a drink after work?"

This is expert advice. I'd take it.

 

[redips]

Thanks, guys! I appreciate your input, as always.

So I just asked a guy out to get coffee. We'll see how this turns out.

 

[HunterM]

BRAVO! Practice makes perfect. Keep asking guys out.

 

[Seasoned]

It's good to go the "speed" dating route. There's no point in waiting weeks only to have nothing come of it.

 

[redips]

So I had totally expected that he would've just disappeared by now, but instead we've been texting a lot, and I think we're gonna plan our first date. I'm actually surprised--he seems really cool.

To be honest, even though I normally consider myself to have above-normal self confidence, I thought this guy might be a *bit* out of my league. Well--we might be in the same overall league--but on paper, he just seems so much better than ALL of my exes COMBINED. I also browse through quite a few profiles, and his is the only one I really like. Most of the other ones are just like, meh... And so he is the only guy I messaged. All of this makes me quite anxious and nervous.

OK, I'm just rambling on right now. Sorry. Dating is just so stressful. *sigh*

 

[eastofeden]

I would do it right away. I always know what I want/like right away so I don't have a lot of rules. If I feel it...I say it.

 

[AstareGod]

Don't get too caught up in thinking he's perfect. Remember, the only information you have on him right now is straight from the horse's mouth. No one, unless they're very open and honest with just about anyone, will really mention anything negative about themselves on a public profile. It's up to you to figure that out on your own and by asking him questions once you both feel comfortable enough around each other. Know what your dealbreakers are and what you can compromise on. The rose-colored lenses only last for so long.

Take things nice and slow and enjoy the time you get to spend with him. Don't rush into anything. Be OK with the fact that things may not work out in your favor. It'll work if it's meant to be.

Good luck!

 

[maxpowr9]

If we set a date to meet up and they bail without extenuating circumstances, I immediately end contact with them. Flaky guys are just not worth the effort.

Even if he isn't dating material, there is potential you could get a good friend out of the ordeal too so it's important to keep an open mind.

 

[redips]

Hey guys. Thanks for all the encouragement.

So we agreed to hang out on Sunday. But now, I'm all anxious about what we should do. I know that many people suggest a coffee as a low-risk kinda thing, so that's cool. But what if (hopefully) things go well. Then what? Movies seem too lame, and they don't provide opportunity for conversation, finding out about each other.

(His profile is quite scant about things that he likes to do, so I can't gather many clues from that). And since we really don't know how this is gonna go, I imagine everything would have to be pretty spontaneous, and unfortunately, I'm not very good at just winging things.

Anyone be kind enough to share some good and creative first date ideas?

-Walking around the city?
-Museum?
-Zoo?
-Short road/day trip?

Oh and then practicalities... I don't at all mind paying and picking up the tab for both of us, but I know if I insist on paying for everything, that might make him uncomfortable, or make him think I'm just trying to get him in bed or something. So what do you guys usually do on a first date? Now since I asked him out, I think I have a good excuse for picking up the tab at coffee/whatever it is that we first do. (This is cool, right? Unless he really really pushes back.) But then what? (Maybe this is really just me... but I really find that splitting the tab on a date is kinda weird...)

Sorry for asking so many juvenile questions. I've dated at least a half of dozen guys in the past, but I'm just feeling really anxious about this one. I really don't wanna mess up.

Thanks, guys.

 

[dragon08]

Since you asked him out be prepared to pay and assume that he expects you to. If he offers say that you can pay, but don't have a tug of war over it. Try to get coffee or a meal at a decent restaurant nothing too fancy. Then if things go well try to go somewhere else, ask if he had any ideas, what is your downtown area like? Is there a nice park to walk through and talk? Is he energetic? Maybe go dancing? Even random places work. Go off of what you guys talk about.

 

[darden]

I usually offer to pay, but if they offer to pay half or insist on paying themselves, I won't protest too much.

on a first date, I usually plan on coffee/drinks, and depending on the neighborhood, either walking around or grabbing dinner if we're not ready to part ways yet.

 

[HunterM]

I prefer active first date activities besides sex.

Depending on the weather where you live, here are some ideas:
Bowling, ice skating, kayaking, stand up paddle boarding, bicycling, rollerblading, bumper car, walking around the city (avoid the ghetto), dancing, bar hopping...

Yes, plan on paying for the first date. It's a gentleman thing to do. If he insists on paying his part of the bill, assuming everything goes well between you two, you can always say, "Today is my treat. You pay for our next date." It opens up the conversation on planning your next date before the first date ends. See how that works? You gotta have game. You're welcome!