How to Ask Someone to Hang Out (Without Making It Weird)

While brainstorming episode ideas, I sometimes search Google Analytics to see what people are asking. Here’s what I found this week: How do I ask someone to hang out without making it weird?

Turns out, millions of people are feeling anxious about asking someone to join them for coffee! (What do I say? What if they think I’m weird? What if they say no?)

Today, we end that cycle. I’ll talk you through how to ask someone to hang out: what to say, how to handle rejection, why it feels hard.

Embrace that awkward first encounter! That’s the kind of thing you laugh about later on, years into a friendship.

In this episode you’ll hear about:

• Why asking someone to hang out feels so much harder as an adult than when you’re a kid or teenager
• The value in being specific when asking someone to hang out and suggesting an activity or time
• The importance of not taking rejections personally! Rejection is of the offer, not of the person; others might not be prioritizing connection right now as highly as you are
• How to make it easier to ask somebody to hang out by choosing an activity they’re already partaking in

Resources & Links

Listen to Episode 145 about reframing rejection with Tanisha Moody, 

Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!

Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

This episode is sponsored by Slowly, a digital pen pal app used by over 10 million people worldwide. If you’ve been looking for a low-pressure way to connect with someone completely outside your normal friendship circle, this is it. Exchange letters at your own pace, no small talk panic required.

Download Slowly free and get 30% off Slowly Plus using my link: https://open.slowly.app/miXL/l8ei5iw6

WANT MORE?

My book, Are We Friends Yet? hits shelves June 16. Get on the waitlist for pre-order bonuses + a first look.

Dive into The Connection Reset. A 10-day private podcast to help you see the abundance of connection that already exists in your day-to-day (Yes. Really. I promise you have more than you realize). Start today. 

Transcript

Podcast Intro/Outro: 1:28

All right, gang. Here's to nights that turn into mornings and friends that turn into family. Cheers. Hello, hello, and welcome to the Friendship IRL podcast. I'm your host, Alex Alexander. Each week we talk about what is working(and what is not) in our friendships, community and connections. Have you ever wished you could sit down and have a conversation about what is really going on in your friendships? Well, you found your people. Join us as we dive into real life stories and explore new ways to approach these connections. Together, we're reimagining the rules of friendship

Alex Alexander: 2:24

You have a great conversation with someone, maybe at pickup or work, maybe at a party, and you're thinking, I really like this person. We should hang out. And then nothing happens, because now you actually have to ask them to hang out, and suddenly your brain is in the situation where it doesn't know whether you are being chased by a cheetah or you are asking a new person to potentially hang out and be your Why does this feel so much harder as an adult? Well, when friend. Full panic mode, right? Your brain is going off. It's we were younger, we could rely on proximity, right? We went to a lot of the same places with our friends, the same school, the same soccer team, the same math club, the same neighborhood. We saw them frequently, just in the places that we went. But something else that I don't see talked about like, what do I say? What if they think I'm weird? What if quite as much is that we weren't wearing as many hats as we are now. We didn't have as many roles in life, and we weren't juggling as many relationships, especially not relationships that we were in charge of maintaining. When we were kids they say no, what if I'm being too much? So you do nothing, and young, kids like middle school and younger, our biggest relationship was with our parents, and that was a relationship that we weren't really responsible for maintaining, or we shouldn't have been responsible for maintaining. We were just kind of there, right? Someone else did the admin work? Our parents thought, wouldn't it be special then when you see them again, maybe you run into them a couple to take little Alex to a one on one movie hang out? Or we should all go on a family trip to make some memories together, or maybe part of our family culture is that we're going to sit down together every night at the dinner table so we can have that of weeks later, you feel awkward, because you both know one on one check in and that consistency our families are making those choices, and they are setting that up in the structure of our lives. Just something to think about now, when we were younger, again, middle school and younger, we maybe had a couple friends, but again, we often saw them in the that you really hit it off, but you're kind of in this same places that we frequented. Anyways, we also had people in our lives who were helping us with the skills necessary to maintain those friendships, right, teachers, coaches. Our adults in our lives, our parents, aunts, uncles, standstill where nobody followed up, and then the cycle grandparents, neighbors, they were helping us navigate difficult conflicts, situations. I mean, sometimes they were literally standing on the edge of the playground being like, Oh, you need to say sorry for that, right? We had a lot of continues. Now that probably hits home for you. It probably guidance, and then what happens? We grow up, we become teenagers, and suddenly some of our most important relationships in our lives are our friends. But again, we are so blessed with proximity in that area or in that time of our lives, right? We're mostly going to the same places as our friends, the same hits home for all of us, because here is what is absolutely wild. math club, the same soccer team, the same school events, the same neighborhoods we can rely on proximity, and these are really the only relationships that we are responsible for, right? Our parents are still supposedly responsible for their relationship with us. Maybe we have siblings, but our parents When I was recently doing some deep dives into new episode are probably helping to shepherd that. Where we're really focused is on how to navigate our friendships, but there are only so many of them. We don't really have all these other responsibilities and roles that we have as adults. We're just ideas, one of the ways that I will go and find episode ideas kids and students, and maybe the math team captain or a daughter, a son, a friend. That's it. There's not a ton there. Now, on the flip side, as adults, we have so many relationships that we are responsible for. You could potentially have a partner, maybe your parents, your is I will kind of go into Google Analytics, and I will look at siblings, your children, older friends, like those childhood and high school friends that I was just talking about. Maybe you also have new friends that you have made in your adult years, and then you have co workers and neighbors, gym friends, book club, friends, friends of friends. You have all what people are searching for. And the honest truth is, these different relationships in your life that you are kind of in charge of maintaining, and that is a lot to juggle now when we add in the fact that societally, I believe we are always kind of taught to put our focus on one relationship as millions of people are literally Googling, searching on Tiktok, being the most important in that time in our lives, which is similar to putting all of our eggs in one basket when we are kids, it's that parental child relationship, which we aren't even responsible for. Then when we become teens, it's really about nurturing those close friendships, and then it kind of searching on YouTube. They are typing in that little box, how stays that way through college and maybe young adulthood, but then there starts to be this real pressure to find a romantic partner, and suddenly that is the most important relationship, And at a certain point you have kids, and then you're often told do I ask someone to hang out without making it weird, which that that is the most important relationship. But you have some marriage counselors who are out there being like, no, actually, the foundation of your family is your marriage, so that is the most important relationship. Put that one first. Like, we can't even decide. Everybody's out here arguing, and I'm just over means, again, you are not alone in this. We are all sitting here here kind of being like, hey, so why can't they all exist? What if, instead of arguing about which one's most important, we actually taught ourselves how to for the first time in our lives, split our focus amongst a bunch of relationships in our life, on our computers, behind our devices alone, trying to figure and simultaneously, when we have the greatest abundance of relationships that we are focused on, we also don't necessarily have the support of proximity. These people that we care about. They aren't all right there all the time. We also don't necessarily have all of the support and feedback that out how to just ask another human to get coffee. Today we're we had when we were younger, right? Like maybe people are going to therapy, maybe people are talking about these relationships with their parents or their friends or a trusted advisor. But it's not the same as when we would come home from high school and sit at the counter and tell our parents ending that cycle. I'm going to walk you through exactly how to about the fight that we got in and get their advice. Ultimately, we are in a stage of life where we are the one responsible. So if you are sitting here wondering, why is it so much harder to make friends as an adult. I hope that you feel validated that it's not you. There is nothing to be ask someone to hang out, what to say, how to handle rejection, ashamed of. It's just that most of us aren't taught how to navigate all of these different factors. And I didn't even mention infrastructure problems, like our lack of third spaces or walkable communities. I have episodes on those, but I'm not why it feels so much harder as an adult, and why the even bringing those. Up here. Like, I think what I mentioned is enough to leave you understanding that it is hard to make friends as an adult for many, many, many people. So with that, let's get into the nitty gritty, practical stuff. awkwardness is actually the best part. So let's dive in. Like, how do you even actually ask a new friend to hang out? There's a lot of debate here. A lot of people say, like, what is better? Should I ask in person or over text? And my answer is kind of like, well, I don't know. What are the circumstances like? Do you have a lot of proximity with this person? Do you see them regularly? Maybe at school drop off. Are they a classmate or a co worker? If so, then sure try an in person ask. But on the So the next practical tip I have for you. Be specific before you walk up to this conversation and ask them to hang out, before you send that text message, think of something to invite them to. And you might be thinking, well, I don't know what their schedule is, and I don't know what they want to do. What they want to do. Pick something. Just pick something. Like, do you always go to the farmer's market on Saturday mornings? Do you think flip side, if you have so much anxiety about asking someone in that it would be easiest to get drinks after work, because you work maybe a couple blocks from each other, and so you could just walk to the middle and meet up? Are you going to a really cool museum art gallery opening? Maybe it's not even a thing that you normally do, like you don't go to gallery openings. That's not the type of person you are, but you got invited to this one, and maybe they want to go along with you, because you don't really have anyone else to go with, or you do. It doesn't really matter. But the point is to just pick something, and I person, you're worried you're going to fumble your words or get it. I get that you want to think of an activity that they have a similar interest for, and you can do that if you know enough about them. But if not just pick something, because we all know the frustration that happens when somebody asks you to hang out and they're just like, hey, do you want to get together sometime? And you'll be like, Yeah, let's do that. And then you're both just staring at each other in a standoff, being say something silly, if that is you then do it over text at the like, Well, what do you want to do? Right? And you're a little frustrated. You're like, Well, you asked me, there is vulnerability in offering up an idea. And so if you are the person who is already being vulnerable and initiating and asking someone to hang out, just go all the way. Just go all the way and offer up an idea at the same time like you're 90% of the way there, just throw 10% in. Now, when you give them that idea, they may not like it, it may not be their interest, but do you know what? It'll lead to? Some sort of conversation, most end of the day. I don't think it really matters. It's just likely like it's so much easier for someone to say yes or no, but it's also so much easier for someone to kind of lean in and let this have momentum. It's a great way for you to be curious. So here's an example, if someone asked me to go to Zumba class, honestly, I'm probably going to tell them no, and it has nothing to do with them. It has to do with the fact that I am terrible at Zumba okay. I am that person that like when everybody is whatever gets you to actually initiate and make the invite going right in Zumba class, I am going left. I run into people. When I was in college, I went to a Zumba class with two of my closest friends, and they knew, they knew that I was not going to be good at Zumba, but they went all the time, and I wanted to go with them, right? I felt like I was missing out. So we were in the back of the class, and they were on either side of me, if you can envision this or like in a row, I'm in the middle because they are literally trying to insulate me from the that is the best way. Okay, so go with that. And I do want to rest of the class, because I kept bumping into them and nobody else. But I did bump into them dozens of times. So if you today ask me to go to. Zumba with you, I'm going to say no, but I probably just told you that story about Zumba and you learned something about me, and maybe I'm like, I don't know. Don't you go to spin class too? Like, I'd happily go to spin class. I'm still the person that stands up when everybody sits down, but at least I'm not going to run into anybody. But add in here that if this person that you want to connect with is honestly, the easiest thing to do would be maybe to go on a walk. Like, would you ever skip Zumba to go on a walk? I really would much rather do that. And do you see how this whole conversation has been so much richer than just do you want to get together sometime by asking them something specific, you have created this whole path of conversation, and now you've learned that I'm terrible at Zumba, I'm uncoordinated, but I would go to spin, but my preference would be a walk. You've learned all of that just because you took the risk of someone that you don't regularly, you don't regularly asking a specific question. Instead of saying, Yeah, we should get together sometime. What do you want to do? And me just saying, I don't know, what do you want to do. So now the next practical tip is to take this a step further. It is to get it on the calendar. Like, if you and I have just gone through this entire conversation and you've said, Yeah, you know, I'd be down to skip Zumba one week and go for a walk. I normally go see, right? You don't have a lot of proximity with them. Maybe to Zumba on Tuesday nights at 6pm and I'm like, Great, let's do it. I can do it Tuesday at 6pm I would keep going. I want to get this on the calendar. I want to lock it down. I want all the specifics. So I'd be like, next week. Yes, next week. Okay, great. Confirmed. We're on the same page. Do I have a way to contact them to confirm? Do I know where I'm going to meet them? Right? If I'm going to meet someone new that I've never met before for a walk? I mean, I guess it depends on where they you met them somewhere, but you're not really sure while live in Seattle, but there is this tiny lake in the middle of the city called Green Lake, and it has a walking path that goes entirely around it. So that's a pretty easy way for me to just be like, Okay, so we're going next Tuesday, 6pm on a walk. Do you want to meet at Green Lake? What if we meet by the boat house at Green Lake? Because that is a well known easy to find lots of parking location for us to go. And maybe they you're ever see them again. I actually have an entire episode come back and they'd be like, Oh, I can't do Green Lake like with traffic and the way the childcare works, I just can't make that work. But we are so much closer at this point to an actual hangout. Just by having a couple minutes of conversation, it saves us from walking away and having to do all this texting back-and-forth of, "What works for you?" "Oh, this week or not next week." "No..." right? Then we have ambiguity of like, well, who's responsible? They asked me to hang out, but talking about initiating with that kind of new friend. It's I'm the one that suggested the walk. Are they the one responsible for confirming the time and the location? Or is it me? I don't know. So the faster you can just get through all the details, like, everything you need to know the who what, where, when. I mean, I guess not why. The why is to make friends, but the who what, where, when, do it. So now let's move on to the risk, the thing that everyone is scared of, which is that you might ask them to get together Episode 123 about the awkwardness of making friends and they might say no, right? So what if you asked me about Zumba and I didn't give all my answers was like, oh, sorry. You might suddenly feel like, Oh, I got rejected. I got rejected hard, but I want to offer you a reframe. Okay, when somebody rejects you, it's not really about you. They're actually rejecting your offer. This is a big mindset shift, one that I'm not going to cover fully in this episode, I would suggest going when you can't rely on proximity. and listening to Episode 145 called Reframing Rejection with Tanesha Moody. It is a really great episode if rejection is the thing that is holding you back. But for the sake of this episode,the best part is that this reframe, even if they say no one time, two times, three times, you have to remember they are not rejecting you. They are rejecting your offer. And you might be like Alex, three times they rejected me, three times. Like that has to be personal. Of course they're rejecting me, to which I would offer you this ready? There are so many reasons that someone could be saying no. Maybe they're busy and their life is just so far past capacity for any added hangouts or friend dates or text messages right now. Maybe they're just really, really in survival mode, and you don't even know. Maybe there's somebody who is really scared of opening up to new people. Whatever it is, it is very likely that their reason actually has nothing to do with you, especially in the beginning, because they don't really know you. We make basic connections with people all the time. We say hello to somebody in the coffee shop. We meet somebody at the farmer's market. We sit down and have a cup of coffee with a new co worker. It is not that hard to allow really simple connections into our life. Maybe we're just chatting with someone after school. We do that with strangers all the time. So if somebody is saying no to you and your first thought is like they don't like me, I want to remind you that we interact with people that we don't really know that well all the time, so it's more likely that there's actually something happening in their life that is making it harder for them to say yes. And I know, I know that that's hard to believe, and I know that in that moment when your brain is in absolute panic mode because you feel like you're being chased by a cheetah because somebody just told you that they can't go to Zumba with you, you don't want to believe me, but that is the reality when you walk away from that moment when your brain and your nervous system Calm down, it's very likely that they were rejecting your offer and not rejecting you like I have no problem just hanging out with you for a little bit, but I don't really want to go to Zumba now. The next question I get from a lot of people is, how many times do I try to connect with someone if I keep getting rejected and there's no right or wrong answer here. I guess it's whatever works for you. I do think you should try more than once, please. Because again, it is very likely they were not rejecting you. They were just rejecting your offer. So try a new offer. A lot of people out there say that three is a good number, and there are some people I know where it's like, let's say they get rejected. Their offer gets rejected twice, but then the other person invites you somewhere, but you can't make it. Like, you can't make it to that party. In their mind, that resets the number of rejections. Like they start over and they will keep trying, but when they hit three and they haven't gotten anything back, they let it go. I don't think there's any right or wrong answer. It's really whatever feels right to you. But I do know there are also people who are like, Okay, so I've made three attempts to initiate. They've said no, and I kind of feel like I got to get to the point of like, okay, I got to take a hint here, and I got to let it go. I would remind you that if you get there and you have to let it go, it's not necessarily that this person doesn't like you, right? Like maybe they're in the middle of a really big health crisis, and they're just not really telling people about it. Maybe they are recently... they've become a caregiver for an elderly loved one, for whatever reason they don't have capacity. So if you write this person off completely, it's just like they don't like me. Then what happens if they come back around in six months a year, two years again, your offer was rejected, not you. Next, let's talk about what happens if you do set a time and a date and a place, and it is now Tuesday at 5pm and we're about to go meet up for that walk, and they cancel. That's a bummer. Okay, I want to give you a big hug, because that sucks. You're probably excited, or maybe you were nervous, and now you're like, I've had all this anxiety all week. Why? My first question would be, did they try to reschedule, like was, was this in good faith? Did they put in some work to try and find a new time? I would take that to heart personally. Now, if they don't reschedule, then here is what I would tell you, you have to remember that this person is just some new person out there in the world, right? They are not someone that you have really strong roots with. So if it doesn't work out, it doesn't work out, and it's not like you're losing a decade long friendship. But that also means that people won't necessarily put in the same amount of effort that they would put into a decades long friendship, and therefore it makes it a lot easier to cancel on somebody, because that connection isn't a huge priority for them. Maybe they're like, I have plenty of friends. This was just like, a nice to have, and I'm just so overwhelmed right now I can't make it happen. But if you listen to what I just said, it wasn't about you, it was about them, right? It was about them feeling overwhelmed in their own life. Now, another one that just really sucks is, what if they said yes, and then they ghost you? My suggestion here would be to reach out one time, one time, and if they respond, approach the conversation with curiosity, because was it really about you, or was it about them? And maybe they just aren't very good at communicating when big, hard things come up, right? You don't know them very well, so you don't know that. Now, if they don't respond, I would just let it go. I know that hurts. I know that sucks, and you may never know why, but. At the end of the day, it's bound to happen like rejection is bound to happen when we try something new. If this reframe about rejection has felt hard, or if rejection is your biggest fear in all of this when it comes to making new friends again, go listen to Episode 145 Reframing Rejection with Tanesha Moody, it will completely change how you think of rejection. Now here is another really big thread that runs through all of this, but I don't think is talked about enough connection, making friends, building community, adding to your village, whatever it is, however you phrase it, that might be a really big priority for you right now, especially if you're somebody who's here listening to my podcast, like you're being intentional about this, but it might not be a priority for someone else, and that shows up in a lot of ways. So one of them might be that you have invited someone to hang out, and maybe they have said yes, but it kind of feels like, yeah, I guess, you know, they're not that invested in this. Or maybe they said yes, but it was just hesitant overall. Or maybe they said no the first time, and then kind of like a maybe yes, like it's kind of a weird Yes. You're getting this weird feeling, and you're like, how do I even really know if they want to hang out with me? Which I would say to you, you don't. You really don't. There's a lot of uncertainty in making friends, but if you can get your mind right about it, and if you can understand why there's uncertainty, I think that helps you move forward, because then it's not necessarily about you. There is a lot of societal stigma about making friends. A lot of people don't even think that expanding their social circle is really an option. They think that they needed to make their friends when they were younger and keep them right, or they think that this is a time in life to be prioritizing their family, their career, their finances, their whatever. If someone doesn't realize that expanding their social circle is an option, then it's probably not going to be a priority, which means that when you ask them to hang out, they might suddenly be like, I mean, I I guess, right, but this wasn't on their radar as something they wanted. Maybe they don't know how they feel about it, because they've never really thought about making new friends. They just closed that door and thought it was impossible. Another thing is that they might have another area of life that is more of a priority right now, like, let's use finances for an example. If you come up to somebody and you're like, Hey, do you want to get together for drinks after work next week? If, in their mind, their finances are such a big priority right now, like maybe they know connection is a possibility, but they have done some reflection and like finances are their number one, they really need to get their savings in order. They are tired of feeling like if they got laid off, or if one big expense, emergency expense, came in, they their whole life would be upside down. They wouldn't know what to do if finances are their biggest priority, they aren't even thinking about the fact that they have an opportunity to make a new friend. All they are thinking about is the fact that they don't want to go spend $40 on drinks at a bar, because money is their top priority right now, and they are so hyper focused on that. Or maybe this is somebody who is working on their relationship with alcohol, somebody who is sober, and then when you ask them about drinks, it really has nothing to do with you. It has to do with the fact that they can't be around alcohol. So it's a great time to remember that. Do you know if they really want to hang out? I mean, maybe they do, maybe they do, but it doesn't even come to the front of their mind. And so now you're probably like, Alex, well, how do I know what people are interested in making new connections and which ones aren't? Because I want to make new connections. I'm going to give you a test. I am hesitant to say that word, but I'm gonna do it. This is not a foolproof test, okay? But if you connect with someone and they kind of give you that weird, yes, that ambivalent, yes, they tell you no, but they're also like, keep asking me, and you just want an idea of, like, how much energy do I keep putting into this, then here would be my suggestion to you, see if they are already going somewhere, like if they're your neighbor and they are already taking their kid to the neighborhood park all the time, then ask them if you can join along, if you can meet them there with your kiddo at the same time, or Maybe your kids are in the same school and they are going to the school fundraiser. Can you meet up with them? Maybe it's a co worker who is going to the holiday party. Is that someone you can meet up with when you're there? Like, can you meet up with someone somewhere where it doesn't require them to change their schedule at all? They don't have to make space, they don't. Have to prioritize you over something else. You are just joining along with something they're going to do now, if they are hesitant about that, then in my mind, maybe that's a sign to not continue to pursue it. But it depends on how curious you want to be, because this isn't a foolproof test. Maybe you ask somebody if you can join them at the park, but what you don't know is that they are in such an intense period of work that this is really the only one on one hour they get with their kiddo all week. Or maybe you want to meet up with them at the school fundraiser, but they are volunteering to run the auction, and they're responsible, so that's like, not really a good time to be trying to foster a new connection. So I would give that test a try, but I would also take it with a grain of salt, and I know that that sucks, and you want me to give you a definitive answer, but unfortunately, relationships and connections just have so much nuance, but I hope that it's an idea that you might try. Now, another way that connection being a priority of yours, but not theirs, might show up is that you might always feel like you're the one initiating. Maybe that means they don't like you, to which I would tell you that that's not necessarily true. Again, it might just be that connection is really your priority right now, it's not theirs, but they're willing to join in. They're willing to go along with it. They're willing to be a joiner if they don't have to put in too much effort. Now, my hope will be that once they're more connected to you, once you build a relationship, you can have a conversation about it and be more upfront that you would like to not always be the one initiating, but there's also no guarantee, like this could be a pattern of that person, and we're just not really going to know until we're further into the relationship. Another option might be that maybe this person's never really taught themselves these skills of being an initiator, and this is truly their pattern. I have some friends like that, and I maintain those friendships. I don't think they're bad friends necessarily. There are other ways that they show up for me, really positively. I've talked about this before. Like, I have a friend. She's not really an initiator, but boy, is she a great planner. If I can get on her calendar, she comes up with the most like, fun, spontaneous hangout ideas, and it really gets me outside of my my shell. And I love that about her, and I feel like that's her way of putting in energy. But it does require me to kind of be the initiator. I have other friends where they fill some really important role in my life, that's okay. I'm okay being the initiator, and that might not be you. I'm not saying you have to be okay being the initiator all the time, but it's just something to get curious about. It might save you a couple friendships. That's not really what this episode is about, though. So let's continue on. If somehow you have gotten through this entire episode, and the thing that is holding you back is the fact that you feel like you shouldn't need to make new friends, or it's shameful to be lonely. Then here is what I want to remind you, we live in a really wild world. Because if somebody wanted a romantic partner, and they started talking about that they would be so celebrated. So why have we made it culturally a bad thing to want to build more friends, to build a support system, to grow our community? Why have we made it seem like, if we don't have this robust childhood friendship network or community that we've just always had, something is wrong with us that is so backwards, so you just have to accept that there is literally nothing wrong with you, there would not be millions of people Googling, How do I ask somebody to make friends without making it weird if other people didn't also feel this way, you are not alone. You are not needy or desperate. It's not pathetic. Wanting friends, wanting more community or connection, is simply a neutral fact, and quite honestly, I think a biological need. You are feeling a call to take some sort of action, similar to if you were hungry. If we go back to the finances, example, if somebody said they wanted to get their finances in order, everybody would celebrate them. So it's time to let the societal stigma go and just do what you need to do, everything I have talked about so far in this episode is really about connecting with someone you barely know, but I do just really quickly want to touch on something that I think is a really common experience for people, which is how awkward it is to ask a friend of yours to do something new. Now whether that is a defined friend, so like a gym friend, a work friend, how do you take a friend outside of the context that you are comfortable hanging out with them, and turn them into more of a present friend, to which I want to tell you that it's going to feel very similar quite often, to asking someone to hang out for the first time, it's going to feel a little weird, because you might be really close to this person, and it might be really easy to hang out with them in one context, right? You are, you are attached at the hip at work. You have no problem hanging out at the gym. You love seeing them at book club, but you want to feel closer to them, and so therefore you need to add new ways to integrate them into your life. You need new ways to hang out, and that means that you're going to have to initiate kind of like as if you are a new friend. And in some ways it feels riskier, because what if you ask them to do activities or to hang out in ways that they don't want to, and then it ruins the context you have. That's unlikely, by the way, but in the other sense, it should hopefully be a little easier, because you know this person, you know details about them. So when you're trying to think of that specific ask, you can know that they're like me, and they don't like Zumba, but they like walking, or they've always wanted to get back into running. They love to hang out and just chill. So you can invite them over for a barbecue. The farmers market is always something they want to do but don't ever do. Or maybe they go every week, and you could join along, like, you know details about them. So although it might be a little weird to ask them to hang out in a new context, because there is no guarantee that they'll say yes, I would hope that there's also a little trust that you will both try and find a way to hang out. The other thing is, if they say no, the good news is that hopefully you know them well enough to be like, Oh, is it the time of day? Is it that activity? Why doesn't this work and you can work together to find a different way to connect? Because the way that you want to integrate someone into your life and like deepen that friendship is by finding new ways to spend time together and topics to connect about where you feel comfortable. So the first step is just to find one new way to try and make it comfortable. But it's going to take time, because not what you usually do. Which brings me to my final, final reminder for you, the awkwardness that you feel when you make a new friend or you deepen a friendship, that's actually the good part, like, if somebody says yes, and then you actually do go on that walk and it's a little awkward, that's okay. It might be, but it's not because you weren't aligned or you weren't meant to be friends. It's not because you don't get along. It's just because it's new. And the funny thing to me when I talk to people is that when we look back on our oldest friendships, the thing that we're often the most fond of are those funny memories from when things were awkward in the beginning. Somehow, now as adults, we want to skip over that phase, and we can't, but we also shouldn't, because the awkwardness isn't a bad thing. It's actually the memories and the funny stories that 510, years down the road, you're going to be telling and loving about your friendship and wishing you could go back and relive. So to close this out, there is literally nothing wrong with you. It's not needy, it's not desperate. It's just neutral to want new friends, and when you make that ask be specific, pick an activity and get it on the calendar as fast as you can. If you do get a rejection, they are rejecting your offer, not you. Try again, and "no" might just mean "not now." If you get a no, it might also be that connection is just not their priority at the moment, but it is yours, and that's okay. Someone had to make the ask, and there are other people you can ask as well. And finally, the awkwardness that you might feel when you make a new connection, that's the good part, like that's what you're going to look back on 10 years from now. So here's your challenge this week, ask one person to hang out, pick something specific, get it on your calendar and report back and tell me what happened. And with that, I'll see you next week.

Podcast Intro/Outro: 42:17

Thank you for listening to this episode of Friendship IRL. I am so honored to have these conversations with you. But don't let the chat die here. Send me a voice message. I created a special website just to chat with you. You can find it at alexalex.chat. You can also find me on Instagram. My handle, @itsalexalexander. Or go ahead and leave a review wherever you prefer to listen to podcasts. Now if you want to take this conversation a step further, send this episode to a friend. Tell them you found it interesting. And use what we just talked about as a conversation starter the next time you and your friend hang out. No need for a teary goodbye. I'll be back with a new episode next week.