Reconnected with this guy - Don't know what to do...

[boltnrun]

Just because you prefer to plan ahead...does that mean you MUST restrict your dating to men who also prefer to plan ahead?

 

Seems like a strange hill to die on.

 

And yes, he was trying to ask you out, but of course with your history with him he's afraid of being rejected. Can you really judge any human for being fearful of rejection?

 

Maybe you'd help him be more of a planner and he'd help you be a bit more spontaneous. Who knows.

 

Be open to a different way of thinking! It could be eye opening.

[Jellybean9]

Just read this... Just go for it Milly.

 

Sounds so nice you guys reconnected after 6 years!

 

He is definitely interested :) sounds relt promising!

 

He has asked you out a fair bit. He may not initaite again as he hasn't got anywhere. So you go to it this him. Show him you are just as interested!!!

 

Hey, if he even springs a spontaneous meet... Why not. Sometimes they make the best dates. You go looking to natural and men like that sort of stuff.

 

Good luck xxxx

[Hollyj]

I prefer some notice too especially since I'm not always free last minute anyway.

 

But most times if I'm not free, I will suggest another day and we'll make a plan.

 

So what ya gonna do milly?

 

Please keep us posted, I've got my fingers crossed this works out!

 

Yup! Milly, I think you should have offered an alternate day; otherwise, he thinks that you are not interested.

[Hollyj]

Thanks, SherrySher! I'll try not to. :)

 

You are making a bigger deal out of it, than it needs to be. Think as if you were trying to set up a meet up with a new friend. Would you be doing what you are doing?

[milly007]

Milly, I think it's officially time to take a deep breath, laugh at this whole thing for a bit, and then pepper in asking the guy when you're meeting up before you get into another cutesy emoji volley.

 

He's tried, he really has. He tried right away, if a bit sideways. I'm not sure I would call his approach smart and clever. More like endearingly clumsy—or, well, frustratingly clumsy, depending on your point of view. Seems, for you, that it's been a touch of both.

 

It's also, I think, pretty typical of OLD, where old-school directness is often replaced by winking and hedging. The whole thing with OLD—the appeal, for many—is that it removes the initial sting of rejection that so many people find terrifying, much the way emojis have replaced needing to find words for expressing feelings with nuance.

 

You no longer have to boldly approach the compelling woman at the other end of the bar, sitting under the tree in the park, reading at the bus stop, and I suspect a lot of under 30 people will go their whole lives without ever knowing how awesome and empowering walking that plank can be. No, she's already swiped right, as have you, and from there you get to enter this totally murky space of the text: quasi-intimate on one level, limited and detached on the other, and an oddly casual and familiar way for total strangers to engage.

 

It's, like, you know, y'all are already friends, maybe more than friends, flirting and creating inside jokes. Even though you don't know each other. Brain explosion emoji!

 

Trouble is, it seems for many (him, you) that that nice little rejection-free zone only makes it harder to directly ask someone out. It feels formal. Forward. At odds with the artificially casual space created by the app. That you guys had matched years earlier only reinforced this false intimacy, and all the interim chatter has created the impression that you already kinda sorta know each other. You two "go way back," as the kids say, and his approach is the approach of someone asking out someone he goes back with.

 

It is, in the end, what it is. It's #datingin2018. Shrug emoji. Laughing with tears emoji.

 

He clearly wants to hang, you clearly want to hang—make it happen and let us know how it goes.

 

Thanks, bluecastle. Your emoji references made me laugh. It's as if you've been reading our text messages! Lol.

 

You're right. We have created a false sense of intimacy. He recently sent me a fairly flirtatious text, which surprised me. I responded by saying, "Wow, I'm surprised you said this (in a good way). Normally you seem much more reserved!". He responded by saying, "You must not know me that well then if you're surprised at me saying this. But I probably seem more reserved via text than in person". I then went on to say, "Well, we don't really know each other all that well, tbh. We've only exchanged text messages. We both know that text messaging only reveals so much about someone. We only get to know someone by meeting in person". And he agreed.

 

And we've had a few conversations about how I "seem" nice and pretty, and he "seems" nice and handsome. We both refer to the word seem in our texts and joke about it because we know we haven't met yet, and until we do, we can't confirm these feelings.

 

But thank you for your input though. I'm going to see what I can do about meeting my old pal in person. Lol

[milly007]

Milly!!!! Halfway down your first post, I was like "What is her problem? Why isn't she going out with him??!?!?"

 

YES, he is asking you out. It is a little indirect, but that's what he's doing.

 

 

 

Too funny!

 

Thanks, Jibralta. I'm going to see what I can do about this to move it forward.

[milly007]

Just because you prefer to plan ahead...does that mean you MUST restrict your dating to men who also prefer to plan ahead?

 

Seems like a strange hill to die on.

 

And yes, he was trying to ask you out, but of course with your history with him he's afraid of being rejected. Can you really judge any human for being fearful of rejection?

 

Maybe you'd help him be more of a planner and he'd help you be a bit more spontaneous. Who knows.

 

Be open to a different way of thinking! It could be eye opening.

 

Thanks, boltnrun. I actually mentioned in one of my replies here that I was willing and open to meeting this guy on a spontaneous whim.

 

I have no issue meeting men spontaneously when the feeling's there and if I'm available. No issue at all. I'm all for it.

[milly007]

Yup! Milly, I think you should have offered an alternate day; otherwise, he thinks that you are not interested.

 

When he mentioned meeting for a bite that one day, I did tell him that I'm game for meeting up soon and having a bite if he wants. He said, "Ok!" and that's it.

[milly007]

You are making a bigger deal out of it, than it needs to be. Think as if you were trying to set up a meet up with a new friend. Would you be doing what you are doing?

 

Nah, I'm fine. It might seem like I'm making it a bigger deal when reading it here, but I'm not. I'll figure it out.

[milly007]

Just read this... Just go for it Milly.

 

Sounds so nice you guys reconnected after 6 years!

 

He is definitely interested :) sounds relt promising!

 

He has asked you out a fair bit. He may not initaite again as he hasn't got anywhere. So you go to it this him. Show him you are just as interested!!!

 

Hey, if he even springs a spontaneous meet... Why not. Sometimes they make the best dates. You go looking to natural and men like that sort of stuff.

 

Good luck xxxx

 

Thanks, jellybean! Yes, it is nice that we reconnected. I'm super happy about it. Would just like to see his cute face in person. Will see what I can do. :)

[Batya33]

I didn't read all the responses. No one should be asking the other person out. You are strangers for all practical purposes. Since he's expressed interest in meeting up and you are a planner then simply say or text "great, I am free ____ -does that work for you?" And if he doesn't act in a mature, reliable way about setting a time and place then yes it is time to move on. But only then. All you're doing is meeting to see if a date in the future should happen. I would put aside the "intimacy" and connection you feel from typing. Tell yourself -and be strict with this so you don't get in your own way by being too nervous or having unrealistic expectations -that you are meeting a stranger to see if it makes sense to go on a first date in the future. That is all and self-talk all you need to to get in this mindset. He is not asking you out or suggesting a date -there are no "signals" -there is simply meeting a stranger --- or not.

 

I would not do a last minute plan with a stranger as I think it gives the wrong impression if you are a planner and if you want to date someone in the future who believes it's important to put in effort to planning a date in advance and who assumes you have a busy, fun, fulfilling life where you don't drop everything for someone you don't know well or a stranger. I was asked to meet last minute -sometimes more than once by the same guy and I would politely decline "thanks for the invite, and I'm busy tonight, let me know when you have time to plan a meet, looking forward."

[katrina1980]

 

Yeah, I really do luv the direct, straight-forward approach - it's a big part of what attracts me to a guy.

 

 

Really? Cause later in the thread you posted you hoped he was still as attracted to you as you are to him!

 

Which would suggest you actually don't need such boldness and directness to become and maintain your attraction.

 

Morello did make a great point re just going with how you feel and if you're not comfortable, then don't do it.

 

But I think this goes deeper than that, as with most things in life, otherwise this thread wouldn't be as long as it is.

 

I'm just gonna toss this out mills, but do you have fears of commitment, relationships, intimacy lurking within somewhere?

 

I only ask because I know people who possess such fears, and the more they like someone, the more fearful they get, many becoming paralyzed (like you) over something as simple as scheduling a first meet!

 

My own brother struggles with this.

 

Something to consider?

[milly007]

I didn't read all the responses. No one should be asking the other person out. You are strangers for all practical purposes. Since he's expressed interest in meeting up and you are a planner then simply say or text "great, I am free ____ -does that work for you?" And if he doesn't act in a mature, reliable way about setting a time and place then yes it is time to move on. But only then. All you're doing is meeting to see if a date in the future should happen. I would put aside the "intimacy" and connection you feel from typing. Tell yourself -and be strict with this so you don't get in your own way by being too nervous or having unrealistic expectations -that you are meeting a stranger to see if it makes sense to go on a first date in the future. That is all and self-talk all you need to to get in this mindset. He is not asking you out or suggesting a date -there are no "signals" -there is simply meeting a stranger --- or not.

 

I would not do a last minute plan with a stranger as I think it gives the wrong impression if you are a planner and if you want to date someone in the future who believes it's important to put in effort to planning a date in advance and who assumes you have a busy, fun, fulfilling life where you don't drop everything for someone you don't know well or a stranger. I was asked to meet last minute -sometimes more than once by the same guy and I would politely decline "thanks for the invite, and I'm busy tonight, let me know when you have time to plan a meet, looking forward."

 

Thanks, Batya. I appreciate what you're saying. I wouldn't exactly call myself a planner when it comes to dating. I do normally like a heads-up and some advance notice. But every now and then, if I meet a guy and I'm feeling a connection, I have no issue meeting them last minute if I'm available. In fact, if they suggest a meet, I'd rather live in the moment and meet them on a whim if I can, to be honest. You know, strike while the iron's hot, as they say.

[milly007]

Really? Cause later in the thread you posted you hoped he was still as attracted to you as you are to him!

 

Which would suggest you actually don't need such boldness and directness to become and maintain your attraction.

 

Morello did make a great point re just going with how you feel and if you're not comfortable, then don't do it.

 

But I think this goes deeper than that, as with most things in life, otherwise this thread wouldn't be as long as it is.

 

I'm just gonna toss this out mills, but do you have fears of commitment, relationships, intimacy lurking within somewhere?

 

I only ask because I know people who possess such fears, and the more they like someone, the more fearful they get, many becoming paralyzed (like you) over somethiing as simple as scheduling a first meet!

 

My own brother struggles with this.

 

Something to consider?

 

I do love directness and a guy that's straight-forward, yes. My interest is still there, but I'm feeling it wane a bit; probably because I'm tired of all the texting.

 

It's funny because, at times his texts seem very sweet and flirtatious, which catches me off guard because more often than not, we're just being silly with each other and enjoying the natural ebb & flow of the text conversation. His flirtatious comments are pretty direct, and I've told him that I like seeing this side of him since he's normally kinda reserved. He's just not as direct when it comes to asking someone out, I guess.

 

Honestly Katrina? I do wonder if I'm a commitment phobe, I really do. I yearn to find and be with someone and have so much love to give, but at times, when I'm presented with a potential partner - and I'm talking really good guys - I catch myself wondering if I'm retreating a bit into my own little shell. Maybe I'm so scared to have my heart broken that I'm avoidant. I don't know. It's something for me to look into though.

 

Interesting that you pointed this out. Can I ask what made you think this?

[SherrySher]

I do wonder if I'm a commitment phobe, I really do. I yearn to find and be with someone and have so much love to give, but at times, when I'm presented with a potential partner - and I'm talking really good guys - I catch myself wondering if I'm retreating a bit into my own little shell.

 

I kind of wondered about that, because you seem to be stopping yourself and questioning this too much.

 

Does it scare you to just text him to meet for coffee today or this weekend? What if you did meet and it went really well? Would you feel relief or fear?

[Batya33]

Thanks, Batya. I appreciate what you're saying. I wouldn't exactly call myself a planner when it comes to dating. I do normally like a heads-up and some advance notice. But every now and then, if I meet a guy and I'm feeling a connection, I have no issue meeting them last minute if I'm available. In fact, if they suggest a meet, I'd rather live in the moment and meet them on a whim if I can, to be honest. You know, strike while the iron's hot, as they say.

 

Yes I love living in the moment and striking when the iron is hot. In dating I had long term goals and for me personally since I didn't want to give the misimpression of being available last minute I prioritized that impression over strike when the iron is hot. I also found that strangers who wanted to meet last minute especially on a weekend night often were looking for more casual arrangements. If it was something like meeting for coffee at the last minute on a weekday then sure (and even though it wasn't a date, when I reconnected with my husband we ended up making last minute plans to do dinner and referred to it in just that way. Certainly if you're cool with being asked out last minute then no need to change that for a first meet.

 

I'd also be very careful about comparing your typing with him to dating or date-like behavior. You're typing back and forth with a stranger to see if you should meet in person and then to see if you click enough to go on a first date. You're way ahead of yourself IMO and that will show -likely in a negative way -on the first meet if you can't take a step back. Or two.

[milly007]

And honestly, the minute that my dad asked me recently about my relationship status made me think twice and become more introspective.

 

He never asks about that stuff!

 

I think he's just plain old perplexed as to why I'm not in a relationship, yet my mom realizes how difficult it can be out there in the dating world.

 

I've often wondered, off & on, whether I have commitment issues. Have also been told by men how surprised they are that I don't seem as attached or involved as their previous dates or girlfriends - that I seem super independent (but maybe to a point where I can seem detached, if that makes sense). I like my space, to a certain extent, I guess.

[Batya33]

And honestly, the minute that my dad asked me recently about my relationship status made me think twice and become more introspective.

 

He never asks about that stuff!

 

I think he's just plain old perplexed as to why I'm not in a relationship, yet my mom realizes how difficult it can be out there in the dating world.

 

I've often wondered, off & on, whether I have commitment issues. Have also been told by men how surprised they are that I don't seem as attached or involved as their previous dates or girlfriends - that I seem super independent (but maybe to a point where I can seem detached, if that makes sense). I like my space, to a certain extent, I guess.

 

I don't think that means you necessarily have commitment issues. You simply might like your space which can work just fine in a relationship. I wasn't someone who needed more space until I became a mom almost 10 years ago. Now I really do, sometimes desperately. Good thing I married a guy who is reserved, needs his space too and gets that he needs to step in and give me childfree time at certain times so I can get space.

[milly007]

I kind of wondered about that, because you seem to be stopping yourself and questioning this too much.

 

Does it scare you to just text him to meet for coffee today or this weekend? What if you did meet and it went really well? Would you feel relief or fear?

 

I'm nervous about texting him, but I'll get around to it. I think those feelings are normal.

 

But if the meet went well? I would be happy and thinking, "Well, let's see where this goes" (that's if it were to go anywhere at all).

[katrina1980]

milly my brother struggles with this same exact thing, which is why I asked.

 

It boggles my mind and breaks my heart at the same time, cause he's such a sensitive guy and really does want a relationship and to fall in love but whenever he meets a woman he really likes, he becomes literally paralyzed to do anything!

 

I've witnessed him having a full blown panic attack just prior to a date with a new womsn he really likes. He ends up breaking the date with a lame excuse.

 

He has no problems making/keeping dates and getting into relationships with women he does not like that much.

 

But even then, when they start pushing for more, he panics and ends it.

 

He had his heart ripped to shreds many years ago by his first gf with whom he was madly in love, which imo is when these fears started manifesting.

 

I love him to death and it breaks my heart so much.

[milly007]

I don't think that means you necessarily have commitment issues. You simply might like your space which can work just fine in a relationship. I wasn't someone who needed more space until I became a mom almost 10 years ago. Now I really do, sometimes desperately. Good thing I married a guy who is reserved, needs his space too and gets that he needs to step in and give me childfree time at certain times so I can get space.

 

Well, it isn't the me liking my personal space that makes me think I might have commitment issues. I wonder about this for a variety of reasons.

[Batya33]

I'm nervous about texting him, but I'll get around to it. I think those feelings are normal.

 

But if the meet went well? I would be happy and thinking, "Well, let's see where this goes" (that's if it were to go anywhere at all).

 

Sure - feelings are feelings. I would just text and say "hey -how are you - I thought we could plan to meet next week. How is ____"/

[Batya33]

Well, it isn't the me liking my personal space that makes me think I might have commitment issues. I wonder about this for a variety of reasons.

 

I understand. Why do you want to be in a committed relationship?

[milly007]

milly my brother struggles with this same exact thing, which is why I asked.

 

It boggles my mind and breaks my heart at the same time, cause he's such a sensitive guy and really does want a relationship and to fall in love but whenever he meets a woman he really likes, he becomes literally paralyzed to do anything!

 

I've witnessed him having a full blown panic attack just prior to a date with a new womsn he really likes. He ends up breaking the date with a lame excuse.

 

He has no problems making/keeping dates and getting into relationships with women he does not like that much.

 

But even then, when they start pushing for more, he panics and ends it.

 

He had his heart ripped to shreds many years ago by his first gf with whom he was madly in love, which imo is when these fears started manifesting.

 

I love him to death and it breaks my heart so much.

 

Thanks for sharing, Katrina.

 

It would be beyond frustrating and heartbreaking to watch a loved one go through something like this; especially when you know they deserve nothing but the best.

 

You would want to help him, but clearly this is something that's out of your control.

[catfeeder]

You're in your own way. You're on a dating site to meet people, not to fluff around with texts. Skip that, propose a time and place to meet. Turning down the spontaneous ask was no biggie, except that you said 'soon' instead of WHEN.

 

The problem with engaging a big text-fest is that you build too much fantasy into this One Guy, and then every vowel becomes a big deal for you. Back up, recall your whole PURPOSE for messing with a dating app in the first place, and go grab a coffee or a burger with the guy to check one another out.

 

If he turns out to be unattractive to you, you will NOT thank yourself for all of this wheel spinning and time wasting and making up rules.