How to keep a woman engaged through text messing?

[Anonymous]

I’ve been texting a few girls and honestly, I’m really just horrible with the performative stuff. The flirting and flirty messages, how to get them interested beyond matching, etc. They’re very pretty women but I struggle to keep their attention. I ask questions. I put a lot of effort in, in hopes to spark a connection, build a little rapport and ask for a date, but either I’m just falling short or they have way more stuff going on than I do at the moment.

I did have one set up a week ago, but of course it fell through the day of, just as I was leaving to drive an hour to meet her. I appreciated that she reached out in time to let me know, but it’s like gosh, what am I doing wrong? Maybe it would be better in person where my personality and confidence face to face can shine a bit, things would click better, but I’d imagine first dates can be awkward and interview like as well with some people.

[HollyK21]

In my opinion dating apps are one of those things that either works out for you or it doesn’t. The definition of insanity is doing the same thing over and over and expecting different results, so if it’s repeatedly an unfruitful experience then just give it a rest and try to meet a woman in-person.


Don’t get me wrong, I fully understand wanting to find the right person already and feeling impatient with the process — I didn’t meet the right guy until I turned 30. It just may not be your time for that yet and if there’s any indication of this it’s your repeated efforts to connect with women only to wind up disappointed. After enough of those disappointments, rejections, and so forth through the same means it just gets to a point.

[Asker]

I will say, I have gone out of state for the holidays, and the dating pool here is so much better than where I’m from, it’s insane. I’ve been able to swipe favorably on so many more women and have already gotten more matches in a couple days than I usually do in a couple weeks at the very least. The only thing is I’m not here permanently now. It’s always something right?

I am being transparent about it though. And I’m also just leaving women nice messages with either a “just passing thru” kind of tone, but I’m open to anything if someone else is. I do plan on moving here hopefully soon. I guess if anything it’s a way to get some sort of reps in. See what works, see what doesn’t, in a better environment.

I’m telling you though, back home, it is awful. Slim pickings.

[HollyK21]

I get it, I lived in a small town in my early 20s, around the time I was trying dating apps and it can really be slim pickings. I just think that after enough failed connections it becomes clear that you should give that route a break. Since you’ve already begun your search in this new city and intend on moving there then hopefully one of the matches you’ve already made will be successful. If ultimately it isn’t though, you should really consider stepping away from the apps. Seriously, I know there aren’t many opportunities to meet women IRL if you don’t live a very “active” life where you’re always going out. It was a total shock when I met my fiancé, I met him completely at random, couldn’t have seen it coming. You just never know.

[Nikki1989]

You can't. Texting is a dead end.