Should I bother messaging him?

[milly007]

I had someone contact me via an online dating app. We actually matched online before, but I deleted the app before we really got to know each other and I wasn’t sure about him.

 

This time he sent me a nice message, we matched, he was eager to meet, and we set up a meet for last Saturday. We had been communicating for about 1.5 weeks now. I had family matters surface Saturday morning, so I asked if we could reschedule for this upcoming weekend and he said he was okay with rescheduling. Prior to heading off to bed, he confirms that we have rescheduled for “next week”.

 

Then yesterday he sent me a message asking how my week was and if I was working hard.

My replies were short...maybe one or two words long because I was stressed.

 

I just noticed now that he deleted me from the app. What’s interesting is that you’re automatically rematched with the same people you unmatch, and he’s already appeared in my matches after he deleted me.

 

My concern is that he may think I wasn’t interested based on my rescheduling of our first meet and my short replies to him lately. He was also intiating the messages.

 

At first I was on the fence about him, but with each message exchanged, my interest grew.

 

I was tempted to send him a message saying “hey, what happened? Was looking forward to meeting you”.

 

Good idea? Bad idea?

 

He just seems like a super respectful guy and I can honestly see him providing me with some candid feedback if I did reach out. I’m just concerned that I’m once again coming across as cold, even though I don’t mean to. Based on what happened during one of my last meets with someone else, where we got caught up in texting and the in-person meet sucked, I didn’t want the same thing to happen here. I wanted messaging to be kept to a minimum.

 

I was even telling my mom yesterday that I think I was meeting this nice guy on the weekend and was looking forward to it.

 

I suck at online dating.

 

Any ideas?

[Zippy2000]

I had someone contact me via an online dating app. We actually matched online before, but I deleted the app before we really got to know each other and I wasn’t sure about him.

 

This time he sent me a nice message, we matched, he was eager to meet, and we set up a meet for last Saturday. We had been communicating for about 1.5 weeks now. I had family matters surface Saturday morning, so I asked if we could reschedule for this upcoming weekend and he said he was okay with rescheduling. Prior to heading off to bed, he confirms that we have rescheduled for “next week”.

 

Then yesterday he sent me a message asking how my week was and if I was working hard.

My replies were short...maybe one or two words long because I was stressed.

 

I just noticed now that he deleted me from the app. What’s interesting is that you’re automatically rematched with the same people you unmatch, and he’s already appeared in my matches after he deleted me.

 

My concern is that he may think I wasn’t interested based on my rescheduling of our first meet and my short replies to him lately. He was also intiating the messages.

 

At first I was on the fence about him, but with each message exchanged, my interest grew.

 

I was tempted to send him a message saying “hey, what happened? Was looking forward to meeting you”.

 

Good idea? Bad idea?

 

He just seems like a super respectful guy and I can honestly see him providing me with some candid feedback if I did reach out. I’m just concerned that I’m once again coming across as cold, even though I don’t mean to. Based on what happened during one of my last meets with someone else, where we got caught up in texting and the in-person meet sucked, I didn’t want the same thing to happen here. I wanted messaging to be kept to a minimum.

 

I was even telling my mom yesterday that I think I was meeting this nice guy on the weekend and was looking forward to it.

 

I suck at online dating.

 

Any ideas?

 

You say you had family problems. Did you tell that and communicate that to him?

 

Your replies were short. (Now, that's just rude)

 

He initialised most of the chat.

 

You reschedule.

 

No wonder he lost interest and moved on. You can send him a reply if you want but don't be too surprised if he doesn't reply.

[milly007]

You say you had family problems. Did you tell that and communicate that to him?

 

Your replies were short. (Now, that's just rude)

 

He initialised most of the chat.

 

You reschedule.

 

No wonder he lost interest and moved on. You can send him a reply if you want but don't be too surprised if he doesn't reply.

 

We hadn't yet confirmed when/where we were going to be meeting last Saturday, until Friday when we he sent me some ideas. Without getting into detail, I asked him if we could reschedule for the following weekend.

 

In terms of my replies to him on Wednesday, it went something like this:

 

Him - Hey Milly, how's your day?

Me - It's great. How's yours?

Him - Good, but it's so hot out today. Working hard?

Me - Always, as per usual.

Him - That's expected in terms of your profession, right?

Me - Yes, pretty much

 

When I responded to him, I had just gotten of the phone with my mom and was stressed about my dad. My dad has recently had cancer surgery/treatment and we're finding out the results of the treatment next week and I'm trying not to freak out. I realize that my texts could have been more engaging/friendlier.

 

Yeah, I see why he lost interest, too.

 

I thought we would just meet and go from there. Clearly I was naive to think that it would happen at this point.

 

If I send him a message though, I don't want to seem crazy. He's already unmatched me, but as I mentioned above, we're rematched with the same people even once we're unmatched. I don't know...I may leave this one be.

 

But thanks for your honest reply!

[Chai]

Hi Milly,

 

I think you should definitely message him. It is too early to have any real reason for either of you not to pursue this. What is the worst that can happen? He will ignore you, or flake... Hey, you tried.

 

He kind of seems like a bit of a flake himself to delete you so quickly, but I really think that if you are interested, you should reach out!

 

Cheers,

chai :-)

[milly007]

Hi Milly,

 

I think you should definitely message him. It is too early to have any real reason for either of you not to pursue this. What is the worst that can happen? He will ignore you, or flake... Hey, you tried.

 

He kind of seems like a bit of a flake himself to delete you so quickly, but I really think that if you are interested, you should reach out!

 

Cheers,

chai :-)

 

Thank you, Chai!

 

You don’t think I’ll seem crazy or needy if I reach out?

[purplepaisley]

I don't think it would be bad at all for you to reach out, but obviously you'll have to expect he won't respond. You are aware of what you were doing, short, clipped texts. After cancelling and rescheduling and the short texts, it's not a mystery he felt you were uninterested. This isn't the first time this guy has experienced flaky women and uninterested women. He has no idea if you're genuine or not. You can improve upon your communication; you have clearly identified an issue. If you're interested and if you have the time, take the time. I know you're stressed, but here's this great guy that can be a bright spot on a crappy day...take the time. If he was aware of the family situation, he could also be moving on because you obviously have some major issues going on and you may not be in a place to date. Give you space...maybe later. All you can do is try, but I'm questioning if you are in a place to date right now with your dad. I think it's worth a try, however, and I don't think it's needy or crazy. You made a mistake. You don't need to text all day, every day, but put in some more effort.

[milly007]

I don't think it would be bad at all for you to reach out, but obviously you'll have to expect he won't respond. You are aware of what you were doing, short, clipped texts. After cancelling and rescheduling and the short texts, it's not a mystery he felt you were uninterested. This isn't the first time this guy has experienced flaky women and uninterested women. He has no idea if you're genuine or not. You can improve upon your communication; you have clearly identified an issue. If you're interested and if you have the time, take the time. I know you're stressed, but here's this great guy that can be a bright spot on a crappy day...take the time. If he was aware of the family situation, he could also be moving on because you obviously have some major issues going on and you may not be in a place to date. Give you space...maybe later. All you can do is try, but I'm questioning if you are in a place to date right now with your dad. I think it's worth a try, however, and I don't think it's needy or crazy. You made a mistake. You don't need to text all day, every day, but put in some more effort.

 

Thank you, purplepaisley. You make some valid points.

 

I was wondering whether I’m in a good place to be dating right now. I was talking to my mom about this, and I was questioning whether I should or not, and we discussed me not putting my life on hold.

 

For the past 5 years, my life has been full of stress. I’ve had a sick brother, who underwent a few major surgeries, to my dad having cancer two years ago, to a new cancer being found in April. I just pray that we receive good news regarding my dad and that he’s cancer free. I should note that I have not told anyone other than my close friends about my dad.

 

I wonder...at what point do I put things on hold or continue dating?

 

If I considered everything that I’ve had on my plate over the last few years, and stopped dating and meeting people, I’d never date or meet anyone and I’d feel stuck.

 

But on the flip side, mentally and emotionally, I wonder if I have anything to give to these guys that I’m meeting, at times.

 

I want to meet someone, settle down and have kids one day.

 

I don’t know. At this stage, I’m just playing it by ear.

[milly007]

Oh man. He just tried to reconnect with me by commenting on one of my pictures on the dating app. Oh jeez.

[Starlight925]

Oh man. He just tried to reconnect with me by commenting on one of my pictures on the dating app. Oh jeez.

 

You sound like you have a negativity surrounding this guy, and quite frankly, he doesn't seem to be anything other than a nice guy.

 

You rescheduled, you spoke to him with a bit of shortness, you didn't engage him in questions like he was engaging you, and now you're saying "Oh jeez" because he's actually trying to reconnect with you.

 

You will scare this seemingly nice guy off with negativity.

 

Who knows why he deleted the app....maybe he was tired of flaky people, and you seemed to have fit into that category for him.

 

Message him back. Explain that you've had a family situation, and let him know that you're excited to reschedule. All positive. Ask him about himself and his week.

[milly007]

You sound like you have a negativity surrounding this guy, and quite frankly, he doesn't seem to be anything other than a nice guy.

 

You rescheduled, you spoke to him with a bit of shortness, you didn't engage him in questions like he was engaging you, and now you're saying "Oh jeez" because he's actually trying to reconnect with you.

 

You will scare this seemingly nice guy off with negativity.

 

Who knows why he deleted the app....maybe he was tired of flaky people, and you seemed to have fit into that category for him.

 

Message him back. Explain that you've had a family situation, and let him know that you're excited to reschedule. All positive. Ask him about himself and his week.

 

Thanks for the input, LHGirl.

 

No, it isn’t about negativity surrounding this guy. I was happy to hear from him! I was relieved that he opened the door for me to communicate with him. My comment was just out of frustration in terms of dealing with dating apps/online dating. Sometimes it feels like a game, even though neither party intends for it to feel this way. It’s so easy for things to be misread/misconstrued.

[limichelle]

Hi Milly,

 

I think you have a lot on your plate and you could try telling him that you have family matters going on. If you still want to meet it won't hurt. Just something simple, like a cup of coffee. You know we don't always chose our timing when someone enters our life that we think would be a good fit.

 

If he liked one of your pictures that's a good sign to re open communication.

[Starlight925]

Thanks for the input, LHGirl.

 

No, it isn’t about negativity surrounding this guy. I was happy to hear from him! My comment was just out of frustration in terms of dealing with dating apps/online dating.

 

Completely understood about the frustration with apps! Just don't make him pay for your frustration. I betcha he feels the same way about the apps.

 

He seems like a nice guy. He asked you out, he was patient with the rescheduling, he tried to rematch with you, and in his texts, he asked questions about you and your work. He is trying to show you that he's not the frustration, he's the exception.

 

Message him with some enthusiasm and let us know how it goes!

[milly007]

Hi Milly,

 

I think you have a lot on your plate and you could try telling him that you have family matters going on. If you still want to meet it won't hurt. Just something simple, like a cup of coffee. You know we don't always chose our timing when someone enters our life that we think would be a good fit.

 

If he liked one of your pictures that's a good sign to re open communication.

 

Thank you, limichelle! I agree. I’ve had circumstances where I’ve met really good guys under trying circumstances, but didn’t know how to handle it when I was younger. Trying to roll with the punches now and learning as I go.

[milly007]

Completely understood about the frustration with apps! Just don't make him pay for your frustration. I betcha he feels the same way about the apps.

 

He seems like a nice guy. He asked you out, he was patient with the rescheduling, he tried to rematch with you, and in his texts, he asked questions about you and your work. He is trying to show you that he's not the frustration, he's the exception.

 

Message him with some enthusiasm and let us know how it goes!

 

Thank you, LHGirl!

 

Also, I added a few more things to my previous response to you...just to clarify.

 

He does seem like a nice guy, and I’d bet he’s extremely frustrated with dating apps! No doubt.

 

I will be messaging him. :)

[milly007]

So I messaged him and asked what happened. He said that he was surprised to see me pop up as a match (since we were already connected), and that we must have been unlinked. Go figure, right? Onward and upward.

[Starlight925]

Thanks for the input, LHGirl.

 

No, it isn’t about negativity surrounding this guy. I was happy to hear from him! I was relieved that he opened the door for me to communicate with him. My comment was just out of frustration in terms of dealing with dating apps/online dating. Sometimes it feels like a game, even though neither party intends for it to feel this way. It’s so easy for things to be misread/misconstrued.

 

I 10000% get the frustration. It's exhausting.

 

As frustrating as it is for us, I bet it's way more frustrating for the guys. Imagine messaging 50 women, to only have 2 respond, and to have 1 of those two be scammers. And 1 to ghost. I'm not talking about you, just the process in general.

 

My advice....if you find someone who will actually engage in conversation, who will schedule a meet, who will work with a reschedule, and who will comment on your pictures....you might have yourself a nice guy there. I'm not saying he's your lifetime partner, but a nice guy.

[milly007]

I 10000% get the frustration. It's exhausting.

 

As frustrating as it is for us, I bet it's way more frustrating for the guys. Imagine messaging 50 women, to only have 2 respond, and to have 1 of those two be scammers. And 1 to ghost. I'm not talking about you, just the process in general.

 

My advice....if you find someone who will actually engage in conversation, who will schedule a meet, who will work with a reschedule, and who will comment on your pictures....you might have yourself a nice guy there. I'm not saying he's your lifetime partner, but a nice guy.

 

I completely agree.

 

He does seem sweet. Since we started exchanging messages this morning, he’s been so complimentary and it’s kinda making my heart flutter a bit.

 

Don’t worry though, ENA. I’m keeping my expectations in check. When we meet there may be nothing there, but it’s nice to feel that flutter every now and then. :)

 

Also, it’s not very often where we get a second chance at something. It feels good. I’m running with it!

[Amalia13]

Um... you're supposed to tell people how you feel and what's going on. That's called communication?

Text him

"My interest grew with each message exchanged. I am really looking forward to seeing you next week."

In another text:

"I have been stress with family matters :-( "

The texts I suggested are open and warm hearted. (and honest, it's what you said yourself)

The "what happened" text you wanted to send, comes across as needy.

[Chai]

hi Milly,

 

Apologies for my late reply - I only just saw your reply. I think that while there is absolutely no guarantee that he will respond favourably, and I am not in your shoes, so I can't read the situation as you can, I just feel like your connection with this guy has been pretty casual and relaxed up and until now and to my mind there is nothing in particular that indicates that he might be antagonistic towards you. It also seems as though this hasn't been going on long, so it could go either way.

 

I definitely don't think you will seem crazy or needy, or at least not to the average person, but put it this way, what do you have to lose? If you don't message him and he has already deleted you from the app, the chances of ever talking to him again are negligible. On the other hand, even if he does ignore you, or flat out reject you, you have done something that is in line with your values of forming a connection with someone you find interesting and attractive, so I feel like it is worth it! And you will grow as a person.

 

By the way, I totally agree with your idea that you should get off text messaging asap and build your connection face to face. In my experience, text chatting online can create all sorts of weird impressions of people that are barely based in reality. They just seem like two completely different people in my experience.

 

Hope it goes well if you decide to message him. Let us know how it goes!

 

Cheers,

Chai :-)

[Chai]

Lol Milly,

 

I replied to your reply without reading the rest of your thread. Sounds like you have been chatting to this guy a bit and the aforementioned bump was a misunderstanding.

 

Happy for you. Enjoy :-)

 

xx

[milly007]

Lol Milly,

 

I replied to your reply without reading the rest of your thread. Sounds like you have been chatting to this guy a bit and the aforementioned bump was a misunderstanding.

 

Happy for you. Enjoy :-)

 

xx

 

Thank you for taking the time to respond though, Chai! I really appreciate it. :)

[figureitout23]

You sound like you have a negativity surrounding this guy, and quite frankly, he doesn't seem to be anything other than a nice guy.

 

You rescheduled, you spoke to him with a bit of shortness, you didn't engage him in questions like he was engaging you, and now you're saying "Oh jeez" because he's actually trying to reconnect with you.

 

You will scare this seemingly nice guy off with negativity.

 

Who knows why he deleted the app....maybe he was tired of flaky people, and you seemed to have fit into that category for him.

 

Message him back. Explain that you've had a family situation, and let him know that you're excited to reschedule. All positive. Ask him about himself and his week.

 

I agree, I got the vibe that you didn't want him until you perceived him rejecting you, then he became the bees knees, he comes back and its, 'ugh...'

[figureitout23]

I completely agree.

 

He does seem sweet. Since we started exchanging messages this morning, he’s been so complimentary and it’s kinda making my heart flutter a bit.

 

Don’t worry though, ENA. I’m keeping my expectations in check. When we meet there may be nothing there, but it’s nice to feel that flutter every now and then. :)

 

Also, it’s not very often where we get a second chance at something. It feels good. I’m running with it!

 

Awesome! Just be yourself.

[milly007]

I agree, I got the vibe that you didn't want him until you perceived him rejecting you, then he became the bees knees, he comes back and its, 'ugh...'

 

I already responded to LHGirl’s post on this. Pls see above.

[figureitout23]

I already responded to LHGirl’s post on this. Pls see above.

 

I did, I just got through the rest of the post, Im super happy you two worked things out.

 

I think maybe you just need to relax and try not to overthink cause that causes over compensation and confusion. Theres no textbook way of dating, were all stumbling through it