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Considering a Road Trip to Meet a Former Student—Would Love Feedback

funkyjam

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Feb 15, 2023
Messages
79

I’m trying to figure out how to navigate a situation that’s developed somewhat unexpectedly. I teach an online music course, and over the past year or so, I’ve been exchanging messages with a former student. She’s 24 and lives in a small, fairly isolated town—one of those places where dating options and broader social opportunities seem limited. Her mom passed away a couple of years ago, which adds a layer of emotional complexity to any connection she makes, including this one.

We first connected through the course I teach. She had written about a couple of artists I also admire, and we briefly interacted on the class discussion board. That was the extent of it for a long time—over a year, actually—until I was revisiting past assignments for a project and happened to come across her name. On a whim, I sent her a friend request on Facebook. She accepted—and surprisingly, she was the one who restarted the conversation.

Since then, our exchange has grown more personal. She’s been open about feeling stuck—financially, emotionally, even creatively. She’s living at home, working with kids, making art, trying to figure out next steps. Despite all that, there’s a sense of quiet resilience in how she describes her life. She jokingly refers to herself as “the main character” in a town that doesn’t quite understand her.

We’ve been messaging regularly. She shared some of her artwork with me, and I sent her a playlist of music I thought she might like. Our tone is warm, a little wistful, sometimes gently self-deprecating. There’s definitely a sense of emotional intimacy forming—even though we’ve never actually met in person.

After messaging for months she writes:

Girl: if you lived in town i’d invite you to the showcase we do at the end of the term!

Me: I’d love to visit one day. That’s great you have a showcase to display your artwork. If you're ever in my city, let me know and I'll return the favor and tell you where I'm playing.

Aaand then I didn't hear from her for many months. I send a couple of messages without reply, and then out of the blue get a brief "Hey funkyjam how are you doing"

I reply a few days later -
Me: Hey, good to hear from you. Been keeping busy, played a gig at the Jazz Festival recently. How about you?

And now back to radio silence on her part. It's been about two months. I feel like we had enough history to warrant another attempt to reach out. The challenges that I've been facing -
  • She lives a 5-hour drive away
  • The almost 30-year age gap
  • We’ve never met in person
  • Moving past the old teacher/student dynamic
She has a sister in my town that she visits sometimes. I’m not sure what the right move is here, and I’d appreciate any honest thoughts on how—or whether—to move forward.

Below in the Spoiler is most of our conversation:

Girl:
hey, i thought you looked familiar but couldn’t remember where from. you taught the history of rock class, right?

Me:
Yes! I’m going through previous terms of the course for a project: I saw yours about Elliott Smith and it reminded me of how much I also appreciate his work. I thought I’d reach out to you here and send a friend request.

Girl:
that’s cool! it was a fun class

Me:
That’s great to hear, glad you enjoyed the course. I’ll post the project results when it’s finished, definitely on LinkedIn, possibly on Facebook. I’m working on entering the data analytics field, and thought this would be a good way to work with the technology. If you’re interested I can let you know when it’s posted.

Girl:
yeah that’d be great

I send it over a week or two later

Girl:
interesting, thanks for sharing! i liked the part about how annoying spotify genres are.

Me:
Thanks, I thought it was worthy of being discussed even though technically, it’s not really part of the analysis. By the way, did you graduate from college? If so, congratulations! Have you started working?

Girl:
I did graduate with my transfer degree, but now I’m taking sculptor because I have extra time and I’m bored. I’d like to go back to school but not really sure what to do and I’m in a lot of debt. I had a job over the summer working for the camp. When that ended, my boss reached out to me and said she didn’t have a visual artist for their youth starts program, and since she knew i was interested in that asked if i’d be interested. so since october ive been doing art with kiddos in a few places it’s very overwhelming.

Me:
Yeah, that’s a lot of driving. At least you’re doing something that you enjoy. Ideally it becomes a significant money maker. I can speak from experience that it can be a challenge to monetize your art. If you’re a creator, social media and websites like etsy can expand your reach, and in theory will eventually lead to a solid career that’s humming along. But it sounds like you may be on the path to becoming a classroom teacher since you’re already working with children.

Girl:
Yeah, I probably will end up teaching forever now lol. Or doing whatever the theater needs. Ive been putting up posters too. Do you not live in town Falls? Is it weird teaching from far away?

Me:
I live in big city far away and have actually never been there. I know what you mean, it is a little weird to teach through the college and not live in the area. Evidently there are a number of instructors who don’t, and some are even out of state. But it isn’t an issue really, although I’m not familiar with the local references. I had to Google the Theater. I imagine they’re the center of performing arts in town, that’s great you’re connected and working with them. My old band tours a lot and it’s fun to see when they have shows scheduled there. I’d like to take a road trip down there to meet some of the people at the college and see the campus.

Sorry for taking a bit longer to get back to you, it's been busy around here. What kind of music are you listening to these days? Any recent discoveries?

Girl:
It’s honestly not the best place to visit, or live, but I’ve been here my whole life and it’s kind of grown on me. I guess the nature is nice, especially if you’re used to a big city. And I like having a close community, even if I don’t really fit in with most of them. I’m like the main character lol

And it’s ok, I’ve been pretty busy too. I mean I’m kind of just listening to the same old stuff. Maybe I’m getting old, just don’t really like most new stuff coming out. I use spotify for music just because I’ve had it for so long and it's what everyone around me used, I know it sucks ok. I just like that it has almost every song I’ve liked, too late now. Anyways, I usually listen to the discover weekly but I don’t usually like it. Sometimes it's really silly. I like Mitski a lot, but I don’t really like her new album besides a few songs. I felt the same about Lana Del Rey’s new album, but it grew on me. I’m sure you get told about new music all the time, easy for you to find good stuff.

Me:
I grew up in suburban New York City, it’s so far removed from a place like your town. I’ve almost always lived in a big city or close to one, I’m not sure I could live in a small town. The close community does sound nice as does the nature, and evidently Smithsonian Magazine recognized it as one of the top small towns to visit. I think I would miss having a lot of people around, culture, lots of options for restaurants to go to, and the variety of things to do. I wonder about what life is like there sometimes since I teach through the college. Sounds like you see yourself there for the foreseeable future even though it has its drawbacks.

I know what you mean about Spotify, I have all my playlists on there and it would be a pain to rebuild them somewhere else. So, Spotify it is. Sounds like you need a new playlist. If you’re interested, I could put one together and send it over. My tastes are all over the place, so it might be an eclectic mix.

Girl:
It really is so boring. My whole life I thought I wanted to leave as soon as I could, but covid, and then the state of the world, and the rent prices, and then my mom died, and then my dad got divorced, and so many other fun things, and it’s just not possible honestly. 21, still living at home. Don’t have the funds to move out in this town, let alone to another one. And that probably won’t change for a while. It’s very depressing, especially because as a kid I saw everyone above me move out as soon as they could. The world just isn’t the same. The only thing I have left is radical acceptance so. If I’m here, cool, I know the whole town by muscle memory practically. If I need to move, great finally. Right now I’m just stuck, so I really don’t have the energy to even care about where I live.

Sorry, that’s kind of depressing. I’d love a playlist. My tastes are also all over the place.

Me:
That’s a lot to deal with in just a few years. I’m really sorry to hear about your mom, that’s a very tough thing to go through. I totally understand where you’re coming from about wanting to move out. I definitely wanted to get the heck out of my parents house my whole senior year of high school and was looking forward to that. But living at home at 21, especially under these circumstances, is far more common now than many realize. You're definitely not alone in this. I think once you pick a direction to go in for school or a career, you’ll most likely get out.

Here’s a playlist I put together. Some are instrumental songs, a few you might already know. I’d be interested to hear what your favorites are.
playlist

Girl writes back, likes the playlist.


Me:
I have a big class this term, 32 students are enrolled. Only 12 last term, it was a bit of an adjustment. Do you have a website for your artwork, or post it on Instagram?

Girl:
no i don’t. it’s really silly, but i kinda stopped posting on socials after my mom died. we never talked anymore, and one of the only ways she saw what i was up to was her liking my pictures and posts. it’s been 2 years. i want to post. i just can’t. basically, no i don’t have the motivation. but i’d like to. sorry, don’t mean to seem so sad lol! i can share some with you if you’d like, i mostly do boring more professional stuff.

She sends over her artwork

Me:
Amazing artwork! I especially like the skulls, there’s a certain warmth to the colors you choose. Thank you for sharing some photos, I like the variety. We do art (or in my case music) for ourselves, there’s no obligation to post it online. For me, music feels incomplete without an audience, though I can't help but obsess over what I could have done better in the final version and cringe over any imperfections. But there’s no timeframe for when you need to post. They’ll be there when the time is right.

Girl:
thank you, i appreciate it. if you lived in town i’d invite you to the showcase we do at the end of the term!

Me:
I’d love to visit one day. That’s great you have a showcase to display your artwork. If you're ever in my town, let me know and I'll return the favor and tell you where I'm playing.

Girl doesn’t reply

Me:
Recent discovery I thought you may be into sends link to spotify

Girl doesn’t reply


Me:
Hey, it’s been a while! Hope you’re doing well. Just wanted to let you know that my old band is playing in town on Saturday night from 7 - 10 pm. They’re kind of a funky rock band and perform in fruit costumes (really). Great bunch of guys. Below are a couple of links for the show:

Girl doesn’t reply

9 months go by


Girl:
Hey funkyjam how are you doing

I write back a few days later

Me:
Hey, good to hear from you. Been keeping busy, played a gig at the Jazz Festival recently. How about you?

And that’s been it. This last exchange was about two months ago.
 
Last edited:

topcat

Tribal Elder
Tribal Elder
Joined
Dec 20, 2012
Messages
1,065

I’m trying to figure out how to navigate a situation that’s developed somewhat unexpectedly. I teach an online music course, and over the past year or so, I’ve been exchanging messages with a former student. She’s 24 and lives in a small, fairly isolated town—one of those places where dating options and broader social opportunities seem limited. Her mom passed away a couple of years ago, which adds a layer of emotional complexity to any connection she makes, including this one.

We first connected through the course I teach. She had written about a couple of artists I also admire, and we briefly interacted on the class discussion board. That was the extent of it for a long time—over a year, actually—until I was revisiting past assignments for a project and happened to come across her name. On a whim, I sent her a friend request on Facebook. She accepted—and surprisingly, she was the one who restarted the conversation.

Since then, our exchange has grown more personal. She’s been open about feeling stuck—financially, emotionally, even creatively. She’s living at home, working with kids, making art, trying to figure out next steps. Despite all that, there’s a sense of quiet resilience in how she describes her life. She jokingly refers to herself as “the main character” in a town that doesn’t quite understand her.

We’ve been messaging regularly. She shared some of her artwork with me, and I sent her a playlist of music I thought she might like. Our tone is warm, a little wistful, sometimes gently self-deprecating. There’s definitely a sense of emotional intimacy forming—even though we’ve never actually met in person.

After messaging for months she writes:

Girl: if you lived in town i’d invite you to the showcase we do at the end of the term!

Me: I’d love to visit one day. That’s great you have a showcase to display your artwork. If you're ever in my city, let me know and I'll return the favor and tell you where I'm playing.

Aaand then I didn't hear from her for many months. I send a couple of messages without reply, and then out of the blue get a brief "Hey funkyjam how are you doing"

I reply a few days later -
Me: Hey, good to hear from you. Been keeping busy, played a gig at the Jazz Festival recently. How about you?

And now back to radio silence on her part. It's been about two months. I feel like we had enough history to warrant another attempt to reach out. The challenges that I've been facing -
  • She lives a 5-hour drive away
  • The almost 30-year age gap
  • We’ve never met in person
  • Moving past the old teacher/student dynamic
She has a sister in my town that she visits sometimes. I’m not sure what the right move is here, and I’d appreciate any honest thoughts on how—or whether—to move forward.

Below in the Spoiler is most of our conversation:

Girl:
hey, i thought you looked familiar but couldn’t remember where from. you taught the history of rock class, right?

Me:
Yes! I’m going through previous terms of the course for a project: I saw yours about Elliott Smith and it reminded me of how much I also appreciate his work. I thought I’d reach out to you here and send a friend request.

Girl:
that’s cool! it was a fun class

Me:
That’s great to hear, glad you enjoyed the course. I’ll post the project results when it’s finished, definitely on LinkedIn, possibly on Facebook. I’m working on entering the data analytics field, and thought this would be a good way to work with the technology. If you’re interested I can let you know when it’s posted.

Girl:
yeah that’d be great

I send it over a week or two later

Girl:
interesting, thanks for sharing! i liked the part about how annoying spotify genres are.

Me:
Thanks, I thought it was worthy of being discussed even though technically, it’s not really part of the analysis. By the way, did you graduate from college? If so, congratulations! Have you started working?

Girl:
I did graduate with my transfer degree, but now I’m taking sculptor because I have extra time and I’m bored. I’d like to go back to school but not really sure what to do and I’m in a lot of debt. I had a job over the summer working for the camp. When that ended, my boss reached out to me and said she didn’t have a visual artist for their youth starts program, and since she knew i was interested in that asked if i’d be interested. so since october ive been doing art with kiddos in a few places it’s very overwhelming.

Me:
Yeah, that’s a lot of driving. At least you’re doing something that you enjoy. Ideally it becomes a significant money maker. I can speak from experience that it can be a challenge to monetize your art. If you’re a creator, social media and websites like etsy can expand your reach, and in theory will eventually lead to a solid career that’s humming along. But it sounds like you may be on the path to becoming a classroom teacher since you’re already working with children.

Girl:
Yeah, I probably will end up teaching forever now lol. Or doing whatever the theater needs. Ive been putting up posters too. Do you not live in town Falls? Is it weird teaching from far away?

Me:
I live in big city far away and have actually never been there. I know what you mean, it is a little weird to teach through the college and not live in the area. Evidently there are a number of instructors who don’t, and some are even out of state. But it isn’t an issue really, although I’m not familiar with the local references. I had to Google the Theater. I imagine they’re the center of performing arts in town, that’s great you’re connected and working with them. My old band tours a lot and it’s fun to see when they have shows scheduled there. I’d like to take a road trip down there to meet some of the people at the college and see the campus.

Sorry for taking a bit longer to get back to you, it's been busy around here. What kind of music are you listening to these days? Any recent discoveries?

Girl:
It’s honestly not the best place to visit, or live, but I’ve been here my whole life and it’s kind of grown on me. I guess the nature is nice, especially if you’re used to a big city. And I like having a close community, even if I don’t really fit in with most of them. I’m like the main character lol

And it’s ok, I’ve been pretty busy too. I mean I’m kind of just listening to the same old stuff. Maybe I’m getting old, just don’t really like most new stuff coming out. I use spotify for music just because I’ve had it for so long and it's what everyone around me used, I know it sucks ok. I just like that it has almost every song I’ve liked, too late now. Anyways, I usually listen to the discover weekly but I don’t usually like it. Sometimes it's really silly. I like Mitski a lot, but I don’t really like her new album besides a few songs. I felt the same about Lana Del Rey’s new album, but it grew on me. I’m sure you get told about new music all the time, easy for you to find good stuff.

Me:
I grew up in suburban New York City, it’s so far removed from a place like your town. I’ve almost always lived in a big city or close to one, I’m not sure I could live in a small town. The close community does sound nice as does the nature, and evidently Smithsonian Magazine recognized it as one of the top small towns to visit. I think I would miss having a lot of people around, culture, lots of options for restaurants to go to, and the variety of things to do. I wonder about what life is like there sometimes since I teach through the college. Sounds like you see yourself there for the foreseeable future even though it has its drawbacks.

I know what you mean about Spotify, I have all my playlists on there and it would be a pain to rebuild them somewhere else. So, Spotify it is. Sounds like you need a new playlist. If you’re interested, I could put one together and send it over. My tastes are all over the place, so it might be an eclectic mix.

Girl:
It really is so boring. My whole life I thought I wanted to leave as soon as I could, but covid, and then the state of the world, and the rent prices, and then my mom died, and then my dad got divorced, and so many other fun things, and it’s just not possible honestly. 21, still living at home. Don’t have the funds to move out in this town, let alone to another one. And that probably won’t change for a while. It’s very depressing, especially because as a kid I saw everyone above me move out as soon as they could. The world just isn’t the same. The only thing I have left is radical acceptance so. If I’m here, cool, I know the whole town by muscle memory practically. If I need to move, great finally. Right now I’m just stuck, so I really don’t have the energy to even care about where I live.

Sorry, that’s kind of depressing. I’d love a playlist. My tastes are also all over the place.

Me:
That’s a lot to deal with in just a few years. I’m really sorry to hear about your mom, that’s a very tough thing to go through. I totally understand where you’re coming from about wanting to move out. I definitely wanted to get the heck out of my parents house my whole senior year of high school and was looking forward to that. But living at home at 21, especially under these circumstances, is far more common now than many realize. You're definitely not alone in this. I think once you pick a direction to go in for school or a career, you’ll most likely get out.

Here’s a playlist I put together. Some are instrumental songs, a few you might already know. I’d be interested to hear what your favorites are.
playlist

Girl writes back, likes the playlist.


Me:
I have a big class this term, 32 students are enrolled. Only 12 last term, it was a bit of an adjustment. Do you have a website for your artwork, or post it on Instagram?

Girl:
no i don’t. it’s really silly, but i kinda stopped posting on socials after my mom died. we never talked anymore, and one of the only ways she saw what i was up to was her liking my pictures and posts. it’s been 2 years. i want to post. i just can’t. basically, no i don’t have the motivation. but i’d like to. sorry, don’t mean to seem so sad lol! i can share some with you if you’d like, i mostly do boring more professional stuff.

She sends over her artwork

Me:
Amazing artwork! I especially like the skulls, there’s a certain warmth to the colors you choose. Thank you for sharing some photos, I like the variety. We do art (or in my case music) for ourselves, there’s no obligation to post it online. For me, music feels incomplete without an audience, though I can't help but obsess over what I could have done better in the final version and cringe over any imperfections. But there’s no timeframe for when you need to post. They’ll be there when the time is right.

Girl:
thank you, i appreciate it. if you lived in town i’d invite you to the showcase we do at the end of the term!

Me:
I’d love to visit one day. That’s great you have a showcase to display your artwork. If you're ever in Portland, let me know and I'll return the favor and tell you where I'm playing.

Girl doesn’t reply

Me:
Recent discovery I thought you may be into sends link to spotify

Girl doesn’t reply


Me:
Hey, it’s been a while! Hope you’re doing well. Just wanted to let you know that my old band is playing in town on Saturday night from 7 - 10 pm. They’re kind of a funky rock band and perform in fruit costumes (really). Great bunch of guys. Below are a couple of links for the show:

Girl doesn’t reply

9 months go by


Girl:
Hey funkyjam how are you doing

I write back a few days later

Me:
Hey, good to hear from you. Been keeping busy, played a gig at the Jazz Festival recently. How about you?

And that’s been it. This last exchange was about two months ago.
What’s wrong with the girls in your local area?
 

POB

Chieftan
Staff member
tribal-elder
Joined
Nov 13, 2019
Messages
1,485
Clearly a shot in the dark.
- 5 hour drive means it's long distance (never seen anyone make it work long-term)
- age gap is huge! Nothing against it, but for long distance it's even worse
- basically the situation warrants online game strategies, with the caveat you've been texting back and forth for a looong time...which is never a good sign when you talk online

I would scratch her as a minor side-project and focus on local chicks like @topcat said.
 
a good date brings a smile to your lips... and hers

Skills

Tribal Elder
Tribal Elder
Joined
Nov 11, 2019
Messages
6,152
i banged a girl one time, and went to visit in another town by plane, but i had banged her before..... And i was younger skills, i would not do that now a days..... (i have a 20 minute distance rule 45 if above an 8)

i disagree with pob on the texting back and forth for a long time (some girls get more invested like that, big example is inmates or me)..... is not the context of "online game" is a former student...
 

POB

Chieftan
Staff member
tribal-elder
Joined
Nov 13, 2019
Messages
1,485
i disagree with pob on the texting back and forth for a long time (some girls get more invested like that, big example is inmates or me)..... is not the context of "online game" is a former student...
Don't know his texting level...if it's not on point, texting too much (without meeting) could be detrimental
 

TomInHo

Modern Human
Modern Human
Joined
Dec 13, 2021
Messages
813
Yo man!

I read your convo with her and somethings stood out to me

To get a better idea on how to move forward, it would be wise to get a better read on where she's at emotionally

Because during your conversation she got very vulnerable by telling you about instability in her home and feeling a bit lost in life

This may seem like you guys are bonding but you need to step back and ask

"What emotionally healthy person dumps all this information on someone they've never event met yet?"

That's not vulnerability, it's a sign of emotional immaturity

And let’s be real the fact that she’s a starving artist only amplifies this. She’s leaning hard into that damsel in distress energy, whether she realizes it or not

Flirting with an older, more grounded man can feel emotionally safe and exciting... until it starts to feel real, then it may become intimidating or confusing for her

Hence why you probably noticed a drop-off when it was finally time to set up a meet

So, to make this work, you need to have patience and be extremely non-needy

Do not push for something more meaningful too fast. It may also be wise to switch up your texting approach.

Right now, you seem too focused on connecting emotionally, but in a situation like this, it’ll probably work better if you keep things more flirtatious and light-hearted

Tease her, make suggestive jokes and innuendo without making it seem like you’re pushing too hard to meet

And if she seems flaky, don’t trip too much about it. Women like this tend to be spontaneous and can flip in an instant

Which means don’t hold too much emotional weight on it. Text, flirt, and if you meet. . .cool

If you don’t, you won’t give a fuck

Because while she’s trying to figure out where she is emotionally, you’ll probably be busy banging a girl just as hot who lives closer to you and is more straightforward
 

funkyjam

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Feb 15, 2023
Messages
79
Thank you everyone for the replies and giving perspective on this. Since she's so far away and much younger, I've been approaching it like a side project that's just kinda hanging out there. But is has been cool to connect with a former student and commiserate with her about the life of an artist. It's likely that's all it'll ever be. There was depth in the conversation so I felt like I should try to figure out how to move things forward, but there may be too many factors working against that though. I figured I'd run it past the experts here.
 

Skills

Tribal Elder
Tribal Elder
Joined
Nov 11, 2019
Messages
6,152
Thank you everyone for the replies and giving perspective on this. Since she's so far away and much younger, I've been approaching it like a side project that's just kinda hanging out there. But is has been cool to connect with a former student and commiserate with her about the life of an artist. It's likely that's all it'll ever be. There was depth in the conversation so I felt like I should try to figure out how to move things forward, but there may be too many factors working against that though. I figured I'd run it past the experts here.
i personally think IF you don't mind the drive you can get her (i personally would not drive 5 hours), i have girls like that, and i don't worry about age differences (that is her problem not yours)

some things to notice (again my own opinion):

- she soft close you... (in other words she hinted a meet)
- I think your texting is good, but i would try to move from facebook to text/ (as a compliance ladder), tell her that you don't really use facebook much you are too busy (she may be a young girl that does not really go much in facebook, gen z are more on insta, they don't really do facebook, so it may be like she is taking long cause she probably log in facebook once a week or once a month)

- i think your texting is fine personally, (i fucked girls in same situation same texting style)

i think she is what i call a vulnerable girl (review my post on vulnerable girl)

- i would advice just to change medium cause you and her keep losing momentum.... (same shit happen to me) but i ended up banging couple of girls, similar situation...


 
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funkyjam

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
Feb 15, 2023
Messages
79
Thanks for the vote of confidence @Skills My concern is coming across too try-hard. She knows I live a five hour drive away, so it seems like a bit much to go there just to see her. I'd have to bundle it in with something else, like I'm heading that way anyway and let's meet up while I'm there. Which I'm not, so I'd have to create that other reason. She has a sister who lives in my city, so in a perfect world, she would respond to what I said about letting me know when she's coming into town, and I invite her to a show I'm playing.

It's been a couple of months since I sent my last message. How and when to re-engage isn't clear to me. My best thought is something like "I saw this thing and it reminded me of you" and send it with a link.

I'm glad you brought up the soft close where she said she would invite me to her showcase if I lived closer. I respond with "I’d love to visit one day. That’s great you have a showcase to display your artwork. If you're ever in my town, let me know and I'll return the favor and tell you where I'm playing." And that's the last message I got from her, as though maybe she was expecting me to take her up on the offer, despite the distance. I may have unintentionally deflated the momentum, and her lack of response afterward suggests she was expecting more initiative from me despite the distance.
 
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