Help I Swiped Right - Help I Asked Him Out On LinkedIn

Episode Date: July 20, 2025

This week your host SJam spills the tea on that one time that she asked someone out over LinkedIn messages...Plus I'll be responding to reactions from last weeks' episode Help, I've Been on Over 100 First Dates and as ever, I will be answering your dating dilemmas.Follow Help I Swiped Right on Instagram, TikTok and Youtube @HelpISwipedRightAnd email your dating dilemmas and stories to [e-mail] to hear them read out on the podcast!

Hello and welcome to How I Swiped Right. Every week I'll be exploring the highs and lows of modern-day dating culture, sharing fun stories for my dating past and answering your dating questions and dilemmas. There'll be new episodes every Sunday, so please do subscribe so that you get the latest episodes as soon as they come out. As this is a new podcast, I would love your thoughts and feedback. I'll really appreciate it if you can leave a review of the podcast if you enjoy it or email your suggestions for improvements to Help High SwipDry at gmail.com. I'd love to hear from you.

I'm also on social media at Help I Swiped Right, so follow along on Instagram, TikTok and YouTube for more content. In today's episode, I'll be responding to the reaction from last week, Help I've been on over 100 first dates, and I'll be launching in to one of those 100 first dates. stories giving you the full story time on how I asked a guy out over LinkedIn because your girl got bored of the apps I had to branch out I went to LinkedIn so I'll be spilling all the tea on that a bit later on and of course I'll be answering your dating dilemmas as well so to start off with

I just wanted to respond to the reaction from the first episode I've been really overwhelmed with the reaction and the encouraging comments that I've got from so many people. So if you've taken the time to write a review or to DM me or write a comment on social media or yeah, anyone that's just giving me their feedback on episode one, thank you so much. It's really mean a lot to me. I'm obviously brand new to podcasting. I'm just doing this myself at home and editing it myself and everything. So it's a big learning curve for me. I've not done this before and I'm just proud of myself

for launching the first episode and getting really great reactions and comments. So thank you so much to everyone that enjoyed the first episode and thanks for joining me today as well. So obviously last week I was kind of asking the question like, is it weird that I've been on over 100 first dates? Is it normal for age 30? I couldn't quite work it out. Amongst my friends, I suppose I thought a bit of a freak that I've been on so many dates in comparison to most of my friends. But I was wondering, are there other people out there that are like me? And I've come to the conclusion since making that episode and since hearing

the comments from all of you guys, there is no such thing as normal. We, all have wildly different dating experiences for many different reasons and that's okay. I've got friends out there that have been on one first date in their entire life and then I'm married to their childhood sweetheart. And I've got friends that have been on like less than 10 dates. That seem to be quite common around that sort of 10 number. And I've got friends that are up there with me in the 100 club. So shout out to my sisters in the 100 club. we are survivors. I feel like we actually need to get like a badge or something for us lot in the 100 club.

It's a very exclusive club, those of us that have got to over 100 dates in our lifetime. And yeah, I'm not ashamed of it at all. I think that's a thing. Some people might think that looks bad or it's embarrassing or I don't know. I just think that's my experience. I asked last week is that weird, but I've now come to the conclusion that I don't mind if some people find that weird or not. It's just been my experience. I can't control why that's happened to me or, you know, the way that's just so been my dating experience,

the way it's unfolded for me, is that I have been single for a lot of my 20s and therefore I have been dating and, you know, a lot of my dates have been from the apps and therefore the first time you're meeting them all you've got to go off is a picture of them and their prompts and your messaging and you meet them for the first time in real life on the first date and you've got no idea there's going to be any chemistry or not so you know I've had I think many experiences where it has literally just been that first date and then oh there's no chemistry or they don't look quite like their pictures and I've just not seen them again. So I've had a lot of that, I think. Whereas my in real life people, where we've met and dated, I think it probably has been more likely that we would have gone on more than one date, possibly.

I actually remember now, I said last week that I met two people in real life this year that I then went and dates with. That was a lie. I forgot. There was a third one, but I literally forgot about him because it was just one date and it didn't go anywhere. I was the other two. We had a little something. One of them, I suppose, we went on two dates, but one of the dates was a whole weekend. I will go into that story in the future episode. And then the other one I had, the IRL meetup, was, is going to form the story time of today's episode. So stay tuned for that later.

But yeah, I forgot about the other guy that I met in real life this year because, you know, met in a pub really lovely guy um he asked me out of my number and we're messaging and over message he kind of revealed or it came up in conversation that he lives with his parents and i just didn't want to deal with that and i already knew in my head that's just not what i want for someone that I'm dating but I felt bad because I already agreed to the date at this point the date was in the diary he's booked the place we were going to meet and I just thought oh I can't say no at this point now I've got to just go through of it but in my head I already had this thing of like this is not what I'm looking for in a partner so we had the date and you know it's a

nice guy but I just knew it wasn't going anywhere so yeah that one I literally forgot about because I kind of written it off in my head already But anyway, my point of all of this is to say that I think one of the reasons why I got to 100 dates is this whole meeting people on the apps and then to the first date you're literally just like is there even a vibe at all? Do you even look like your photos?

There's so many things about attraction and chemistry that you can only gauge once you meet them. So if you're meeting someone, from an app, it's very hard. You have to go into the first date, just very open-minded. And that's why I think drinks are a good first date. It's kind of like then you can just leave whenever you want to, you don't waste too much time. If anything with the apps, I kind of see the first date purely just as verification. And then it's like the second date is kind of the real first date in some ways. I don't know. Let me know if you agree of that.

but alas I'm in the 100 club and I put out a poll to see how many first dates have you been on in your life because I was curious and yeah the results of my poll so far are 40% of people have been on less than 10 first dates 40% have been on 10 to 50 10% have been on 50 to 100 and 10% have been on more than 100 so that poll is still open on Spotify if you want to comment on it and react to the poll yourself and give your thoughts. But I was just putting out there. I was curious to know what is everyone else's dating experience? But of me, having over 100, this is what's led me to create this podcast because I have got so many stories about my dating experience. So here we go. We're going to dive into the first story time. Help. I asked him out on LinkedIn. So LinkedIn guy, let's dive into it. Right. So a bit of context.

Actually, in general, I have a really big fear over asking people out and I don't think I've ever asked someone out in real life. I really want to grow in more confidence in this you know a lot of times you see someone you make an eye contact and I'm just kind of hoping that they come up to me and I have never made the first move in my life and I'm ashamed to admit that I would really like to is something that I'm striving to do

to get more confident And I think just making this podcast, it's only been two episodes, but the moment after I recorded episode one, even before I put it out there, I felt so much more confident just in general. So I think hopefully in the process of making this podcast, I'm hoping that I'm just going to become a more confident person in general. And then that will translate, not just interdating, but I think one of the side effects will be that I feel more confident. approaching a guy in real life or giving him my number in real life. But in this instance, this is where I gave someone my number over LinkedIn. So I chickened out a little bit. I wasn't quite brave enough to do it in real life. But I regretted not giving him my number in real life. So the only way I had to contact him was LinkedIn. So LinkedIn it was. Right.

So back to the start, I met this guy at a networking event. So I was there and I remember when I noticed him in the room, I immediately thought in my head, he's attractive. Like I noticed him, I clocked him in my head and I thought he's an attractive guy. But I didn't think anything of it. I didn't even think necessarily that I would speak to him. It was a really big networking event. so I was chatting to other people and, you know, I didn't even know if I would speak to him. Anyway, I remember later on that day, I did somehow get talking to him.

You know, you're in different circles, we're chatting to different people. I got introduced to him or I can't remember how we start talking exactly, but I got to talk to him and we were chatting and we actually got on really well. and we then kind of ended up spending the whole day together so I say networking event it's like a whole day thing so yeah we spent the whole day together and we just got on so well we had so much in common and we're just having a really interesting chat so we're getting on well and i think he's fit but we're at a networking event so I didn't know it was appropriate to make a move but I did think it was appropriate in our networking event to exchange contacts on LinkedIn so that's what we

did he was saying there was some event he's running he's got coming up and I was like oh yeah I'd love to come to this um he's like cool work how should I send you details I was like oh yeah let's add on LinkedIn. Looking back, why did I say that? I definitely could have just given him my number here in a professional manner. I could be like, oh yeah, just text me the event. I could have just said that. Anyway, for some reason, I said, let's connect on LinkedIn. And he did send me the event and we were connected on LinkedIn. So now I'm on LinkedIn and I can see his LinkedIn profile and of course I'm having a look for it. And on his profile, and on his profile, while I then see his graduation year, which I can't remember what that year was now, but

anyway, it indicated to me that he was young, okay? I saw his graduation year and I thought, oh, that means he must be younger than what in my head I thought he was. And I've worked out that he's got to be around like 24, 25 and I was 30. So I thought, oh, that's a bit young. wrote myself off. I just thought, he won't be interested because I'm old and he's young and I just kind of like dampened that thought down. I just thought that's it in terms of like the thought ahead of my head of do I try and ask him out or anything. I just thought, I actually he's probably just too young. But anyway, we're still talking. It then goes into like the reception at the end of the day at a drink's reception. We're having a drink there.

And we've both then got a go and he goes, oh, I'll walk you to the station. Again, I was like, oh, that's kind of like making a move. But I just thought, yeah, that's really nice, thanks. He walks me to the station and we say goodbye there. And again, like, he didn't ask for my number there. I didn't ask for his number there. We just said, it was nice to meet you, like, have a great day. Hope to see at this other event coming up.

So that was it. And I walked away from it being like, oh, I didn't know if he was going to ask me out or not, even though I saw his age. And at this point, he might have seen my LinkedIn and I've seen my graduation year. But anyway, walked away thinking, oh, that was a nice day. I met some nice people. That was cool. A few days later, I'm still thinking about him.

And I'm still like thinking in my head, oh, damn it, why didn't I give him my number? as uming and a-ing still about the age thing but the fact that I was still thinking about it a few days later made me think do I ask him out on LinkedIn so of course I asked my girls in the group chat for advice what do I do and they were like you've got to go for it you've got to ask him out on LinkedIn and is the only mechanism I had of contacting him so I was like okay I can do this but I was so nervous because I didn't want to be, you know, blacklisted for like, I don't know the word, it's like harassment on LinkedIn. It was a very, you know, when you meet someone in that context, it's like a professional networking thing, it feels weird, doesn't it, to segue it into dating or, I don't know, I'd love to hear from you guys actually, like, how did you meet, how, how, what's been the weirdest scenario that you've met?

someone you've dated or the weirdest way you've asked someone out I'd love to know um but yeah I was conscious of it being a professional thing and thinking of God and I'm older than him and I didn't want him to feel like harassed by me because I couldn't quite tell the vibe what he was thinking but anyway finally over March deliberation I plucked up the courage to message him on LinkedIn and I just something like, hey, you know, it was great meeting you the other day. I don't know if you want to grab a drink sometime. If you do, here's my number, but no pressure of not. And I thought, oh my God, it's done. I've actually given some my number. Even there's a bit of a chicken because it wasn't in real life and I did it over LinkedIn. I did it. And yet, thankfully, he replied

pretty quickly and said, yes, like he would like to get a drink. So I was like, thank God. And he doesn't think that I'm like harassing him um so then yeah we had um our first date he booked a wine bar and it was really nice again we got on well and I appreciated that he kind of booked the first date and took the lead after that point because I had kind of gone out there and asked him out so I appreciated that after that point he kind of like took the lead and we were talking about it on the date actually about this whole, well, his age and the LinkedIn thing. And he was saying how, yeah, he thought that there was a vibe too, but he wasn't sure. And he didn't want me to feel like I was being harassed by him. Um, so he didn't ask me out. And I was saying, yeah,

like, I had thought about, you know, being a bit more flirt with you or asking you out, but I saw your age and I thought oh he just won't be interested because I'm an old lady but no actually turns out we were both interested and yeah we did get on really well and we had you know a series of I would say about five really fun dates but things just didn't continue after that and that's okay that's what dates are for it's for getting to know people and getting to see if there is something more there and yeah things didn't continue but at least I had the experience of asking someone out on LinkedIn and it going well so I'm not advocating this I'm not saying to you all now go out there and start sliding into the DMs on LinkedIn I'm not giving that out as advice

okay I actually did meet him in real life first I think there are some people out there that have just messaged on LinkedIn without even meeting them. They've just seen, oh, they're fit in their LinkedIn photo and have messaged on LinkedIn. I have not done that and I don't advocate for that. But if you've really met someone and there's a vibe and you've got an overweb contacting them, you've got to do what you've got to do. Okay? Like, sometimes the dating apps, they just get boring.

Like I said, I've been there, done that. you've got to branch out. There's different ways of meeting people and how fun to meet someone in real life, to ask them out, or be at Overlington, and then date and have a good experience. I say this because it is becoming more rare, I find these days, that you do meet someone in person and that there's a connection. It does tend to be the apps these days. And I've noticed now that men definitely ask people out less. I'd love to hear your thoughts on this. And if you're a guy listening to this,

please comment in as to have you noticed this? Like, when's the last time you asked someone out in real life? Do you find you're meeting people in the apps more? And I say this because looking back to when I was 18 and the apps didn't exist, me and my friends would probably go out most weekends, as we do, 18 years old, just started going out. We were reminiscing. and saying how every week, every time we'll go out, we would get numbers.

Were there people wanted to message or not? We were getting interest, okay, numbers every week. And that was just normal and we thought nothing of it. And again, as I said, whether there are people that we found attractive and wanted to date or whatever or not was another question. But it was just normal. Now, it's so rare that a guy will come up to you and give to you his number in real life. I don't know if it's the COVID effect, I don't know if it's the apps.

A lot of men I spoke as well saying it's just like, you know, the Me Too movement and they're scared. Even LinkedIn guys said this to me, like he didn't want me to feel like I was harassing him. Equally, I was scared that he might think I was harassing him. So I think there's a bit of fear now in today's culture about making the approach. It's obviously in some ways it's a good thing because it's that. understanding of consent and not wanting to harass someone. And, you know, that's obviously, it's good to be considerate of that. But I hope we're not losing out on those real life meetutes as a result of that. Because, yeah, if someone asks them out in real life,

I'm never going to be mean or anything. It's just the way you do it. And if you do get a no, just accept that and move on. Don't you. keep pestering someone. That's when I would say that's not cool. So yeah, a bit of a reflection there actually on just asking people out in general. So tell me what's the weirdest way or weirdest place that you met a romantic interest? Have you ever slid into anyone's DMs on LinkedIn? Have you met someone at a networking event before and it's turned into to more afterwards. Email me at help I swipedry at gmail.com and I'm Help I Swiped Right on Instagram, TikTok and YouTube. So this is the part of the show where I answer your dating

dilemmas. So let's take a look at this first dilemma. This one is about experiencing anxiety over getting slow replies when texting. So I've been single for nearly a year and I've met this new guy on Hinge. We've been speaking for a month and he has my number. He usually responds to me in the same day, but the gap between me messaging him and him responding is normally rather long, brackets, unless he's actively online, which I don't know because he's got his active status turned off. Okay. We haven't met in real life yet, but we're both expressed an interest in doing so. I'm very new. to dating and am I getting worried over nothing? Right. There's a few problems here. The first one being

that you've been speaking for a month and you've not met yet, why? What's the point? Okay, I'm sorry, girl. What is there left to say at this point? No wonder the replies are slow because you've been speaking for a month and you've not met yet. The meeting needs to happen ASAP, okay? I would say, and again I do this, I said earlier, I don't ask people out in real life, but I've got no problems doing it over Hinge. And if I've been messaging someone for a while, I have just said, look, are we going to meet soon? Or when are we meeting? Because, yeah, we're not just going to keep texting for mum, that's wild.

So that would be my first put of call. I'll just bite the bullet with him and just say, look, I'm free this day and this date. are you free then? Would you like to do X, Y, Z? And just get a date in because this messaging can't go on. But on the other hand, I do hear what you're saying about slow reply anxiety and I have experiences in the past, but never when it's someone that I've not met yet. When I've not met them yet, I don't feel anything at all because, you know, I've got nothing to base it on. We've not met. You're just something when I'm messaging. So I think at this stage, no one owes anyone anything. And that's my opinion. I'd love to hear from you guys. What do you think about the

etiquette of when you're just in the messaging stage on the apps and you've not met yet? What do you owe to each other at this stage? In my mind, pretty much nothing. Unless you've arranged a date, then I think what you owe each other is to go on the date or if you can't make it anymore or you don't want to go you have to say that with enough notice and don't ghost that's what I think is owed to each other so I don't think he owes you fast replies but obviously the connection the conversation the banter can be hard to build if the replies are slow so I completely hear what you're saying there but girl always Also, there's plenty of all fish in the sea. You're on a hinge. There are obviously loads of people out there.

If this guy isn't really, you know, meeting your vibe of how often you want to communicate, maybe you're not the right partner. But saying that again, it's really hard to know at this stage because you're not met. That could just be him. And it could be that he replies quicker once you have met in real life. or he could just be bad on the apps and not as a notification's on. There's so many reasons into this slow messaging thing. So you could even just raise it with him actually and just say, oh, you know, hey, I prefer to speak more frequently. One idea as well could even be to offer a phone call rather than just messaging.

Say, oh, hey, you know, I've noticed our replies are a little bit slow. I don't know if he'd be up to doing a phone call sometime or just up for meeting sometime and actually going on a date. That's what I would say. I completely get the slow plier anxiety. I think when you do like someone and you've met and you've started to build a connection and there's been a change in their replies

and there's suddenly becoming slow at replying. At that point you obviously are thinking, oh, have they gone off me? And yet that's not a nice feeling. But for the most part, yeah, on the hinge messaging stage, that's just like is what it is. So good luck, girl. I think just bite the bullet and try to meet up with him, ASAP. If he is still a bit avoidance, still not really applying to you, you've got to move on. Next dilemma. Hey, I became single in 2023. I went on a few first dates last year, but to be honest, I wasn't in the headspace for a relationship. I have now downloaded Bumble and Hinge as I finally feel.

like I have time for dating again, but my nervous system is already activated. I'm 26, I've been in one relationship and 10 first date overall, so don't feel experienced, which is from where, which is where I think all the nerves come from. I also know change triggers a lot of anxiety for me, but also know I don't want to stay living at home with my mum. Let me know your best advice for getting out there sifting through the weird profiles. I've legit paused the app within 24 hours as I already feel so overwhelmed. Brackets. P.S. I've had so much therapy.

So definitely need to put that interaction now. Okay. Yeah, dating nerves. I completely get why that would feel nervous when you've been in a relationship and you're just getting back into dating again. It is scary. It is really anxiety-inducing. That is a normal reaction because, especially from the apps,

you're about to go meet a stranger and have to make conversation from nothing. I mean, obviously, you'd been messaging on the apps a little bit, but it's really daunting. And obviously, you want to make a good impression. You're worried about, do I like them? There's a safety worry as a woman as well when you go out and meet a stranger. So some advice for you as someone who's been on 100 first dates now and I've gone through those nerves a hundred times

Saying that actually, it depends of you obviously at this point I don't always feel nervous. Sometimes I feel nervous for a first date but the nerves go up and down I think there was times where obviously last year I was going on so many I felt nothing at all and that was bad because you should be feeling a bit of excitement about going on a date because it is fun, it is exciting. But I think last year I was doing so many, I'd lost that feeling of nerves and excitement completely. I just felt nothing at all. I just didn't

care anymore. So don't know why I was going on them. But anyway, what can I say for advice about nerves and anxiety? I think, think to yourself, is there anything the person you're meeting could do to alleviate your nerves, would having a phone call or a face time in advance help you? Would making it a daytime date and doing something a bit more casual help you? Last week, I poo-poohed coffee dates and they're not for me, but maybe for you, that is something that you might feel more comfortable. Or do you prefer to have, you know, a drink and have alcohol to calm the nerves a little bit? In which, because I think that's absolutely fine, just do whatever it is for you that's going to make you feel more comfortable, which as I said, it could be

meeting up in the daytime, a little lunchtime date maybe, or an afternoon drink or a walk or an activity. Activities can be quite good as well because then that kind of helps with conversation. Like maybe you could do like those interactive darts things or mini golf or whatever it is. That could be quite a good first date. Yeah. So to have a think about what what environment do you feel calmer in? And is there anything that he could do to help of your anxiety? And of course, the other piece of advice I've got to give is you've just got to get out there and do it. Once you've had the first one, your nerves will go down.

It's because of that gap. I remember I felt the exact same way when I had to start dating again after my relationship ended. and the first one, I was absolutely breaking it. Because at this point, yeah, it's been years. You've been with something you felt so comfortable with. You've taken some time away to process the breakup. You start dating again. And it's really scary.

And you're probably not even ready at that point when it's the first date. You know, you have to just get through the first few ones as the process. And then your confidence will build as it goes along. So good luck. and well done for being brave and getting out there. This will be the last dilemma that we look at today, so let's jump in. Am I being too clingy? Looking for advice on this.

My boyfriend and I live about 45 minutes apart, both in London and have full-time jobs. What would you say is a healthy amount of time to see each other weekly? He only seems to make time for me if it involves his or my friends, friends, as we don't have a lot of one on one time, or many date nights, just the two of us. I'd ideally like to see each other once or twice a week, quality time, and one of us stays over at the others. He says he needs to go to the gym three times a week and has stressful work, so he hasn't got time for this. I look at my friends and their boyfriends, and they seem that they see them fairly often and I've cute

date nights planned. This is all I want really. I've bought this up to him that we might not be compatible in this way or be fulfilled in what we're looking for in a relationship. He has also said that he broke up with his ex because she became anxiously attached

and clingy but now I wonder if she had the same experience. I really like this guy and I've tried to bring it up to him that he just spirals and we end up arguing. Any advice? oh this wasn't a nice one to read sorry that you're going through that that is tricky and yeah you shouldn't be feeling that way I don't think that's being too clingy at all I think wanting to see your boyfriend um but at least once a week just a two of you is normal in my opinion and like you say once again everyone's different

he obviously doesn't want that so he might be more compatible of a partner who doesn't want that. I'm sure there are for people out there that are happy with seeing their partner less often. But certainly for me, I would like to be seeing my partner, like you said, once or twice a week. And of course there's times we're doing group things, but like you, I do value that one-on-one time as well.

And having date nights. To most of you, the date nights I don't care about as much on, like I'm very happy just chilling at home with a partner as well and then you know having the old date night weekend break like that's all fun and I like that but what I care more about is the one-to-one time I don't really care what we're doing like I said it could just be chilling at home absolutely fine with me but I think having that regular one-to-one time is important or phone calls and bringing up phone calls again so I'm people out there hate phone calls. I know this, but not me. Obviously, I've got a podcast. I'm a yapper, but I love a phone call and a FaceTime. So if I'm not able to see my partner, you know, as often as I would like, or they're busy or they're away, then I certainly like a phone call or FaceTime instead, and that helps me feel close to them. So how do think about if that would work for you as well? What is it that you're looking for? Is it the being close,

Is it the catch up? Like, would you feel happier if you were having phone calls instead? Or do you just need to see him more often? And that's fine. So what I'm saying to is you're not being clingy. And if he responds to this by just having an argument, that's not good. Okay? You're not asking for anything unreasonable.

I think you could try saying it one more time and just say, look, it's really important to me in a relationship that I like to see my partner. Often, can we work towards seeing each other at least once a week? Do you for example of that? If he says no, I think you've got to end it. I'm sorry to say that, but, you know, you shouldn't be feeling unhappy. You're young, you've both got full-time jobs. You're both living in London.

He's got the gym and stressful work. But, like, you should be having hobbies as well. You've got other things going on in your life. completely get that. You've both got things going on and you've got to make time to each other. But that's the point. Is it the gym three times a week? That's fine. Okay. Where else can he make time to see you? That's not much of an ask for a partner. That's my answer to that dilemma. We'd love to hear what you guys think. Please write in to help I swipe dry at gmail.com. Right, that is everything today. Thank you so much for listening. If you enjoyed today's

episode, please leave a review. It would mean absolutely well to me. Remember that you can send your dating dilemmas to help I swiped right at gmail.com and follow the podcast on Instagram, TikTok and YouTube. Thank you so much for listening. See you next Sunday.