So there's a guy...

[jenny01]

Hi,
So I've been dm-ing with a guy friend of mine. I used to like him in high school. And I got jealous when he got a gf. He's single rn. We've been talking for about 3 months, but we really haven't talked about anything really deep. I think I like him. But I don't actually know. How do I find out if he even thinks of me like I think of him? I've invited him over to a couple parties I've had but he's been working both times. What should do?

[Elise]

Hi jenny01, I hear you that it can be hard to infer how someone is feeling over texts and dms, body language and tone convey a lot that is therefore be missing or unclear in those settings.

Perhaps then, a good place to start is to take the opportunity to reflect and delve a bit deeper into what you might be feeling, and what you might like from a partner. This kind of reflection can help us better understand whether we're feeling a desire to have a connection with someone, rather than that person in particular, if that makes sense?

So, with that in mind, there are a couple of things I'd like you to read and think about, and then let us know what you think, if you're comfortable with that?

• Do you feel an emotional connection with this person? Like they could be a friend and that you can talk about shared interests, values, etc. and are they someone that you trust or are building trust and emotional intimacy with, even if topics are yet to get "deep"? Or do your conversations feel more surface level?
• Read the below articles, and let us know the thoughts/questions/curiosities that arise. It is okay to not have all the answers, maybe it will prompt more questions that we can talk about here:
  • Supermodel: Creating & Nurturing Your Own Best Relationship Models
  • Hello, Sailor! How to Build, Board and Navigate a Healthy Relationship
  • Embracing Newbiehood
  • How to Understand, Identify and Make Choices About Desire

Looking forward to hearing what may or may not resonate with you in these articles, and hearing your thoughts as you feel comfortable sharing them.

[jenny01]

I met this guy when I was in 8th grade and we weren't really friends until we were in high school. We used to be good friends. We both knew who each other liked. And we used to hang out at our youth group together. My friend always said we'd end up together and we'd always deny it.

When we were in high school, he got a gf. I wasn't expecting this. I always teased him about having a gf bc I knew he didn't have one. But when she showed up, I got jealous. One time, I had to spend like 2 hrs with him, his current gf, and his old crush. That was not fun. We always used to be on the same playing field. Neither one of us had ever been in a relationship. So his new gf changed things.

I haven't really hung out with him since maybe 10th or 11th grade. Covid and changing churches didn't help. When I got IG we followed each other. One day his mom posted that he got mono. I was thinking that she posted that to punish him. Most kids don't follow their parents on IG so I hit him up and asked him if he had seen what his mom posted. He had and he told me that he didn't actually have sex with anyone. We started talking. We've been talking for about 3-4 months. I like talking to him. He's always been fun to talk to. But am I only remembering high school him?

We both have big families with lots of younger siblings and we are both Baptist Christians. We have the same friends. Rn our conversation are very surface level, but I'd like to go deeper.

Since I haven't hung out with him for so long, I don't know what he wants. I've never been in a relationship before, but I'd like to be in one. I know he'd understand that if I had family problems, I'd have to spend time with them, since he has the same situation. He knows I prioritize school and I know he prioritizes work.

I just don't know how to get beyond where we are rn. I feel like if we hung out in person that would help, but he's really busy with work. And if he did ask me out over dm, my parents wouldn't like that. They don't really know I'm talking to him. I really hope that he can come to one of my parties, so that my parents can know him. Bc I really hope that we can get beyond the friend zone.

[Sam W]

Hi jenny01,

I hear you saying you want to better understand how you feel about him, and see how he feels about you ad like you may only know the high school him. To me, the best option is to keep getting to know the current him, which it sounds like you're already doing. If you wanted more than just chatting over text, what if you opted for being very direct and asking, "hey, I'd like to hang out (or even facetime/skype/ect) with you. If you want to do that, what works with your schedule?" Does that feel doable?

You mention that your parents would likely distrust him if he were to ask you out. Since you two were friends for a few years previously, did they ever meet him then?

(This is just an aside, but someone can get mono without every having sex).

[jenny01]

When he had mono, I tried asking him if he wanted to play video games together or play battleship and facetime, but he lives in the country and only has so many things connected to wifi. So he didn't have his xbox connected and he didn't have battleship. And I have asked to come to some of my parties, but he's been working.

They knew of him but they never really met him. They knew whose son he was, if that makes sense.

And yeah he told me that he didn't know how he got it.

[Sam W]

Since the parties seem to conflict with his schedule, what if you tried just inviting him over one on one? That way, you two would get to spend some time together and you'd have a chance to introduce him to your family? Or, if you have friends in common, maybe inviting them plus him to just hang out one day?

[jenny01]

Well I'd want him to come over first when I had other friends over, so that my parents would now who he is. And it's really hard to have friends over now that school has started. I'll still have my parties, but it's not like I can just randomly ask my friends to come over and hang out bc they have work and school too. That's why I have the planned parties, so they can try to fit it into their schedules.

[Marisha]

Then it sounds like you know what to do! Ask your friends when they would be available for a little get-together at your house and loop him into the plans.

I'm of the opinion that when a connection has potential, all people involved will put into making time for one another. I wonder, have you considered just asking him outright if he likes you?

You also asked in an earlier reply if you're just 'remembering high school him' when you're enjoying talking to him. Are you wondering whether this is a relationship you'd actually like to pursue, or something else? What do you want from him?

[jenny01]

I haven't asked him. We haven't even hung out yet, so it'd be weird if I just dm'd him and was like "hey do you like me?"

I would like to try a relationship with him.

[Marisha]

Oh, fair enough. You do have a history of knowing him in person (I assume, since you mention going to school/church together), so maybe you can feel comfortable going there with him since you've known him a while?

Do you know if he's looking for a relationship right now? Maybe you can find out through a mutual friend.

[jenny01]

Yeah we knew each other from church. And idk bc we just started talking after like 2 years.

Idk if he's looking for a relationship. And just like I haven't talked to him for two years, I haven't talked to any of our mutual friends either. We've all went our separate ways. We don't have youth group every Wednesday together anymore.

[Sam W]

In that case, I really think it'll just be a matter of continuing to talk with him and the two of you getting to know each other as you are now; there's not really a way to rush that process, so patience may end being the key here (as will being okay with the idea that you may not want to be in a relationship with him after all as you get to know him better).

I do want to circle back to something you mentioned earlier; is there a reason he'd have to come over with other friends in order to meet your parents?

[jenny01]

Yeah. My parents wouldn't approve me of talking to him online and getting to know him that way. Like if he asked me out over dm and they hadn't met him yet, they wouldn't approve. Which sucks bc that's like the only way I can talk to people since I can't drive and meet them places.

[Mo]

Hopefully there will be a time when he'll be able to attend one of your parties! You could even ask something like "I know you couldn't make the last couple of these I hosted and I'd like to include you, is there a time you know you'll be free that i could plan one?" That might give you a better chance of planning something he'd be able to make it too.

I do think, too, that Sam's thought of spending some more time chatting and continuing to reconnect is a good thing to focus on for now.

[Sam W]

I do want to add that, unfortunately, it seems like the things that were impeding your ability to date or meet people--namely, your parents behavior--may also get in the way of you getting to know this guy as well. I also strongly suspect that, even if he were to show romantic interest in you, they would come up with lots of reasons why you couldn't see or communicate with him, you know (it may help to look at how they responded to your siblings dating) ? So, while you should keep building your friendship with this person (assuming it makes you both happy), I think it's also helpful to reality check yourself now and then on whether you're in a situation where you could freely pursue the kind of relationship you want. Does that make sense?

[jenny01]

To Mo,
Yeah, hopefully I'll be able to have a bonfire this month. I'll ask him first when he's available.

To Sam,
Well my older sister didn't date until she was like 26. Which sucks, bc my parents want me to have a relationship like my older sister's. My oldest brother has been in a lot of relationships where he's gotten hurt and my mom doesn't like that(I don't like that he's gotten hurt either), and my mom didn't like other older brother's previous girlfriends. When he was in college, he did meet his wife tho. My younger sister wanted to ask this guy(one of our friends) she liked out a couple years ago, but my mom said no bc she wanted the guy to ask. I knew that he prolly wouldn't ask my sister out bc he's a really big introvert, but he liked my sister back. Since, my sister didn't ask him out, they grew apart when he left for college. My mom wants them to get married and it's infuriating. It's like maybe they would've if you would've let my sister ask him out! It's the freakin 21st century!
And yeah that makes sense.

[Sam W]

That does sound infuriating! It also sounds like your parents are actually doing a similar with dating (both for you and your siblings) that they've done when they talked about wanting you to be independent; they say they want it to happen, but they put so many conditions on it that they're functionally preventing it from happening . Too, it sounds like they may also cloak those attempts to make sure you or siblings only date who they want you to in "caring" language; yes, it sucks that your brother got hurt in relationships or when relationships ended. But part of navigating relationships, romantic or otherwise (and, honestly, part of navigating life) is accepting that sometimes you be disappointed or hurt. That's sort of the risk we all take when we form a bond with someone.

You mention your parents want you to have a relationship like your older sisters'; have they given you any sense of what that means? Are there certain things they've suggested you look for in a partner?

[jenny01]

It is very infuriating. They try to keep us safe, but it's really too safe. They don't let us make our own mistakes and learn from them.

Well she didn't date until she was like 26. They want our future spouses to be perfect. My older sister is the perfect child. She didn't date in high school, she was the first to get married, first to give my parents grandkids. She's annoying really. I like never talk to her bc when I try she ends up criticizing me.

Well they want him to be a Christian and get along with our family. I already had that in mind tho. It's just so annoying that they compare everything I do to my older sister.

[Valerie J]

Hi Jenny,

This sounds so exhausting and frankly misleading. If they truly were trying to keep you safe, part of safety is learning on your own and creating independence so you have knowedge to make decisions in the future. Like you said, they don't let you learn from your mistakes which is a crucial part of growing up and becoming an adult. Control does not equal safety. It can often lead to less safety. Be very careful with the ways they use that word.

Being compared to siblings is a very difficult thing to deal with and can be harmful because fundamentally you are not your sister. You are your own unique person who is going to live your life differently because you are not a clone. Your family will need to learn that at some point. And of course it will put a strain on your relationship with your sister! Your parents are stunting both your ability to grow and learn while simultaneous causing more internal issues within the family.

One way you can remind your family of that fact is by focusing on who YOU are. In what ways are you similar or different from your sister? What are things you are proud of about yourself? What kind of relationship would make YOU happy - not anyone else or any societal expectations?

[jenny01]

I have told my parents before that I don't need them to keep me "safe" anymore. I'm going to be 20 soon. They won't let me get snapchat bc they want to keep me "safe". But in reality that's hindering me from keeping in touch with my friends.

I am a very unique person. I have never gone along with what everyone else was doing. I have asked my brother to help me with the situation with my parents, but he says they won't listen to him.

I am very different from my sister. She's also 13 years older than me and thinks everything I do is stupid. I told her that you can learn some really cool stuff on tiktok. She disagreed. Then one time she found a recipe on tiktok she liked and wouldn't even tell me that I was partially right. She's very millennial. She won't let her kids have anything normal bc she thinks it'll hurt their stomachs. It's like they'll never know if they've never had it!

Things that I am proud of myself are that I am really smart, I'm very ambitious, and I never let people tell me I can't do something. I will prove them wrong.

And idk. If the guy I'm interested in does ask me out, it would be my first relationship. I really want someone to love and who loves me. I think the guy I like isn't happy tho. He works all the time. Like all the time. And he never has any time for fun. How do I convince him to take time for himself? I asked him if he was happy the other day and his response was Define happy? That is not a good response.

[Sam W]

Those are all awesome things to be proud of!

I also feel like comparing you to your sister is extra-strange given the age difference; you two of growing up in wildly different social circumstances, on top of, you know, being unique people with different needs and wants.

I agree that response suggest he's not feeling great right now. If the two of you are friends I think it's within bounds for you to comment on what you've noticed. It might help to be specific; so, if you notice he always sounds tired or sad, or like work is eating up his whole life, you could mention those things. He may not open up right away, but even just letting him know you're here to chat if he's feeling stressed or sad can be really helpful. Does that feel like conversation you can have with him?

[jenny01]

Yeah especially with my older siblings, it's so frustrating to be compared to them. Like we grew up in such different time periods, that my parents try to parent me and my younger siblings like they did my older ones. It's like we don't even have the same circumstances as them.

And yeah I'm trying to get him to open up. I really want him to be happy. How do you start to have deeper conversations with a guy?

[Valerie J]

Hi!

I think it would be helpful for you to approach this mentally as if you are talking to any of your friends. The gender of the person on the other end doesn't have to change the dynamic. With any relationship there are a lot of ways to deepen a friendship! One way is finding out common interests or hobbies and getting into more detailed conversations. What fun things are you passionate about? Sharing our passions is such a great way to connect, expand our interests, and demonstrate an actually interest in what someone is saying. What's music you like to listen to? Media you engage with? Hobbies? Sports? Anything can fit. It also can inspire you both to do one of those things together.

Another way is by offering emotional support if that's something you feel like you have the capacity to do. It sounds like he works a lot which can be exhausting, offering emotional support to talk about stress in his life or things that might be upsetting him can also deepen a friendship. Take the time to try to listen to what he's feeling and expresss your solidarity and aid. Let him know you're here for him. And for some people that's all they really need to hear. That they aren't alone. Friendship is built on mutual trust, a sense of community, aligned interests, care, and A LOT more.

Also sharing about yourself is another way to make another personal comfortable. It's hard to be vulnerable but it can open a lot of doors for you.

What were some ideas you had in mind for talking to him in a more deeper context? What have you already talked about? Is there something you wish you could share with him?

[jenny01]

I want to talk about starting a relationship. I've asked him for advice about what do in the friendships in rn. I wish I would've listened to him, bc now it's gotten out of control. We've also talked about my epilepsy which I'm pretty sure he didn't know about. We've talked mostly about work and school tho. I really want to tell him I like him, but I don't know how he feels and I don't want him to stop talking to me.

[Valerie J]

Okay. I think its a really good idea to take this slow right now for a lot of reasons.

Mainly, one of the biggest communications he has sent is that he is really busy right now and even friendship communications have been a lot for him. I think giving him some time and trying to understand who HE is is really important right now. You've indicated you wanted to be closer friends but then immediately jumped to wanting to start a relationship. I think that first step should not be ignored. It's really important to have a good understanding and mutual trust in a relationship before it becomes more romantic. Like you said, trying to jump into your feelings for him and desire for a relationship has the potential to disrupt the friendship you have right now. If you truly feel like you're close enough right now then you can maybe ease into trying to communicate your feelings. But I would really suggest just a little more time.

Additionally, what would dating realistically look like for you right now? Beyond inviting him to your parties, what are ways you'd actually be able to see him? Anticipating that your parents are going to attempt to get in the way probably under the guise of safety, what do you have planned to advocate for yourself?