So, I’m back at it attempting to date once in a while here. To be honest, my divorce proceedings have derailed me in many ways in continuing to date consistently. I really thought I’d be done by now with it. Still, I’ve been more active of late to stay sharp, but why is it so hard?

Rule 21: Text Communication Is Tricky

In the last post, I outlined the importance of meeting in person, which is definitely key in actually dating someone. Still, I have really struggled of late with communicating with women. In this era of digital communication, so much of what we do to get to know each other is via text or chat rooms on the apps. Now, there is a ton of benefit to communicating this way. Texting and/or messaging is an on demand medium. What I mean by that is the message is there to respond to when I am able to do it. Now, I’m a guy who comes from the pre-messaging era. So, I typically will respond almost immediately to any text or message I receive. In the end, I believe that is both polite and important to respond as quickly as I can, but also to keep the ball in the air so to speak. In fact, message communication reminds me of this game we used to play as kids we called, “Keep Off.” The idea of the game was that we had a balloon filled with normal air, not helium, and we would sit or stand in our family room and try to make sure the balloon never touched the ground. Hence the name, “Keep Off” to keep the balloon off the ground. I feel like communication is the same way, especially with texts. Like the game, you hit the balloon up in the air to your other player like a text to someone, and then the other person has to hit it before you hit it again, but before the balloon hits the ground (when you have lost interest). Otherwise, you are literally playing the game by yourself keeping that communication and this figurative balloon off the ground.

Before I get into my experiences here, I wanted everyone to understand once again how these apps work. If you are on Hinge, then you can start a communication with someone via liking their picture or even making a comment on their responses they have in their profile. The other person has the opportunity to “invite you to chat” or literally respond to your comment – in both instances you both enter a chat room on the app itself to communicate. For Bumble and Tinder (and other apps like Coffee Meets Bagel), you both have to “like” each other via a swipe or pressing a button to put you into the chat room. Then, depending on the app, either person can initiate a conversation (Tinder and CMB) or on Bumble the woman has to. It’s just a gateway to actually get to communicate.

Once you are in the chatroom, it is up to the both of you to play Keep Off, basically. However, here in lies the differences between men and women often. I think it is still expected that the man would drive conversation. As I put in other posts, I do encourage anyone to be clear in their intentions in their profile, because there are a lot of people that may just be into chatting and not actually meeting. From there, ideally, you will set up a date and move off the app to texting with your phone number or hell, even calling someone.

In the past year, I have learned that it is not great to hit someone up a second or third time without a response on the apps. Otherwise, you seem stalker-ish or maybe desperate. I guess I’m the kind of guy who doesn’t have shame in trying again after a couple of days or even a week. I call that the “Ping.” The Ping is a check in that you can make on people, not only potential dates. If you haven’t heard from someone in a while or maybe your circumstances changed and you want to re-initiate conversation, then you Ping them to see how they are doing. This act shows you are interested, of course, but it is really just an attempt to start the Keep Off game again. What’s weird to me is that I’ve often matched with women, especially on Tinder who literally never respond to you. I mean a message is not a marriage proposal or anything more. It doesn’t hurt to try again if someone is busy or maybe they are so inundated with responses (like my female cousins) that your original message went to the bottom of the queue, by the way, not my issue – I have very few active conversations.

The Look On this Guy’s Face Tells It All

Now, I do struggle with communicating with new dates. This week’s story will outline 2 different communications with women I’ve had lately. Both equally frustrating.

Person 1: So, we matched on Hinge almost a month ago. In fact, I was pretty excited to meet this person. It took a bit to get her to respond initially, but after some time we have had some regular chatroom messages. Now, this person travels a lot for work, so despite me asking their availability to meet in person a couple of times, she has been out of town each time. I have told her that I would be patient for her, and in the interim get to know her better on the app. The other key fact is she has sent me messages from time to time asking an open ended question (an open ended question is one that cannot be answered with yes or no or a quick answer – that’s from my sales training). Usually, it is a How question, like “How was your trip to Florida?” or something. Sure, she can just say “Good” but it is open enough she can elaborate. Regardless, I thought that we were at a point that meeting is a near certainty. Last week, in fact, I invited her at the last minute to see Avengers: End Game. Of course, she was out of town, but it was a humorous reply that I found playful, always a good sign. So, this week (mind you 1 month since our initial messages), I asked early in the week – “Are you free this weekend any days from Thursday-Sunday?” She replied, “Thursday.” I responded, “Ok cool, I’m free after 7:30 PM. Let’s meet!!” She replied…….I’m still waiting for a response. Now, I’m going to admit that I need a person to be interested in me to actually go on a date. Maybe she was waiting for a plan for the date. Maybe she has plans already. Who knows, but I fully expected some kind of response here like, “Let’s do it!” Or “I’d love to.” Instead, I’m sitting here thinking, should I text again? I’m a stubborn Capricorn here, and I feel like I’ve asked this type of question for about a month now. It’s not my job to play Keep Off with trying to meet up. So, it appears as of this post that I will not meet her. C’est la vie. This is where you have to set your own limits on what you are willing to put up with and how long to wait.

Person 2: I’m sure this person will love that I wrote this, but here goes. I actually had a very nice date with this person the other week. We had a lovely dinner and enjoyed seeing a play. I thought the date went well overall, and I was interested in seeing her again. I did text her the next day. Then, since the following day was Easter, I thought I’d wish her a Happy Easter. We exchanged a couple of texts. I will say that I usually do not text someone after a first date every day, but with the holiday, I made an exception. Come Monday, she initiated a text during the day about Spring being here – which now we know wasn’t true…I replied, “Hope it lasts” or something along those lines. Now, in my defense, that particular week I had some plans already for my weekend, plus my daughter was over come the weekend, so I was not going to push hard for another date yet. Plus, work was busy and I had a lot of prep for my coming divorce hearing, so I did not text her on Tuesday or even Wednesday. Like a good dater, I go on the apps still every day to keep prospecting. I mean we had one date that was nice, but just one date. I noticed on Wednesday that my date had already unmatched me on Bumble….. I probably jumped the gun, but I took that as she was done with me. I found this really strange, as it was only 2 days prior we were texting, and we only met on the app one week before. Needless to say, I’m not going to communicate with this person again or even Ping her. I feel like she made the decision for me.

Here lies the differences between men and women, I guess. It seems like women want you to be into them, right from the jump, but when they are ready for you. Person 1 clearly had some mild interest, but not enough to meet me in person. Person 2 expected me to either set up another date within 3 days or she didn’t like my response when she initiated. My co-worker, a woman, told me she would be salty with my response to Person 2. I, honestly, didn’t understand why? I played Keep Off!! I responded. It wasn’t even a question, it was a statement about spring – yes a reference to my profile. From discussing this with my co-worker, she said that it is a big deal for a woman to initiate conversation with a guy. I have to ask why. It’s not like I gave her a one word answer like Person 1 here. Or in Person 1’s case, I did initiate to meet and then she just sat there.

I wish I had the answer to how to handle the situation better, but on the one hand, I seem like coming off too pushy and desperate, and the other I’m some a-hole who doesn’t want to talk to you. I guess there is a balance you have to find in communicating in these early stages. I mean the investment for both parties is low at this point. It is much easier to keep swiping and find someone who behaves the way you expect in lieu of directly communicating with someone about where you are with things or even demanding clarity.

So, I will continue the trial and error of dating. I would love to here your stories about this very thing and opinions on who these interactions should happen.

Wegs