Don't wait too long to ask someone out

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This point mainly applies on dating apps.

There is a balance. You don't want to ask someone out too soon (i.e. in the first few messages). They want to get to know a little bit about you and find something they have in common with you first.

But a lot of guys (especially ones with less confidence and less social skills) make the error on the other extreme. They intend to spend 2+ weeks with them building rapport through long messages before meeting.

The issue with this is that people may not want to spend weeks texting someone and investing to them only to realize that they have no chemistry when meeting in person.

This is especially true for women who get lots of matches. If a guy waits 2 weeks to ask her out on the date, by then she could've gotten 10 more matches and gone on 2 dates.

If you have something really interesting to bring up through text, go for it. But it's also fine to just use text to set up a date, and keep texting minimal until the first date.

Back when I was less socially apt, I felt like I had to text them every morning for X number of days. And looking back on it, it just felt like an awkward routine. Are you sending that "hows your morning going" text because you really enjoy doing it, and that's what's really on your mind, or because you feel like you need to ping them every 24 hours or else they may forget you're alive?

A female friend of mine made a good point. There are guys who try to hook up the same night. And on the other extreme, there are guys that want to text for weeks and be penpals. But where are the men that have the courage to ask women on real dates?

Every person is different, but generally the sweetspot seems to be
* Get their number in the first 8-12 messages (or no longer than 3-4 days)
* Schedule the first date within 3-4 days of matching with them (no longer than a week)

You think more than a week is bad? Hahahaha. I could tell you stories. As a lesbian on dating apps who often gets stuck in the talking stage, I have definitely fallen into this trap before. Plenty of times. Ugh.

I'm working on it. Trying to keep my conversations more focused. It's a nightmare though, constantly opening. I've had a couple of dates but there just wasn't any chemistry. We're still friends though who talk on social media.

I don't get flirting honestly. I think I just friendzone myself at the best of times.

I only ever once tried one of those free dating sites and that was around a decade ago as someone persuaded me to do so as he wated to join as well.
No one lived anywhere near me (Talking 100+ miles away) so I thought I would try messaging someone by saying "It is quiet on this site" and no one talked. No one replied at all! I quit the site after a few weeks as it was pointless me being there. Women don't talk though. If I was a woman dating a man men talk so it would be different. I don't know why women who don't reply are on dating sites as it is totally pointless!

I know that was a long time ago and this is in hindsight, but:
* Use the most popular dating sites/apps; niche ones have smaller populations
* Your location is a factor. If you're in a small town in a remote area and you're not near a city, it is harder to get replies.
live an area with less than, say, 50k people
* If you're not getting responses from women, it's because your pictures are bad. Men need to take time to learn about photography, take lots of pictures, pick the best ones. If you're serious about finding a partner online, you should spend at least 50-100+ hours focused on improving your pictures.

At least it's better you find out there's no chemistry sooner rather than later.

I kinda have difficulty not knowing what to say in the first few messages of conversations too.

To me it seems like the most important factor is that they like your profile. (i.e. photos of good quality, photos that show your personality, photos that are conversation starters, and listing hobbies/interests in your profile.

Everyone's different of course, but I feel like, to most people, their interest in you comes down to:
1) You have a great profile
2) Your text conversation is okay enough.

It probably doesn't even have to be a special conversation. Maybe you have something in common, can ask open-ended questions/ share a conversation, and no obvious redflags.

I wonder if people even care too much about the first few messages anyway. To me it just seems like (a) if you love someone's profile, you'll try to meet them even if the initial conversation isn't amazing and (b) as a way to vet obvious redflags before meeting (i.e. the person is really rude in the conversation, etc).

I agree. If you wait too long to ask someone out, another person might ask them out.