Trying hard to be interesting and cute

[Alex39]

So I got a message from this guy on Facebook. He had seen me post in a group we are both a part of. We've been talking on Facebook messenger for a few days. We are the same age and we seem to have a decent amount in common. He's mentioned maybe we can grab dinner some time. But no plans yet. He seems nice. Has a good job. Seems genuine. I googled him and he checks out. 

 

He asked what I was doing this weekend. I mentioned I have a big family thing to go to. I was wondering if he was going to ask me out. But sadly I'm busy already. He messages me daily but I feel like I'm so boring. I answer his questions and I'm uninteresting. I try to be flirty here and there, but I don't want to be too flirty like I just want to hookup. I feel like the conversation is so dull and he isn't enjoying speaking to me. I don't know what to do. I ask him questions too. But I think I'm nervous and I feel like I'm so basic. 

[lostandhurt]

Is this who you really are or is it because you are holding back trying not to say the wrong thing?

Be yourself, talk about what interests you, what your day was like.  Remember he will meet you sooner or later and get to know the real you so why not be yourself with some extra on top and see how it goes.

Everyone is on their best behavior right off but eventually you revert to your daily self. Don't be afraid of bringing up something you are passionate about just because you think he will not think it is exciting.

This is who you are so you might as well put the real you out there.

  When a guy you are interested in asks you out or if you are busy this weekend and you are busy always offer another day you are free.  This shows him you are interested and are actually busy but want to see him.

 Lost

[jul-els]

Be yourself. Always. Anyone who’s worth your time will like and appreciate it. Anyone who isn’t worth your time, won’t. Simple. 

[Batya33]

Yes - I hope you suggested an alternative day -if he asked you out not just what you were doing this weekend (or do what I did a couple of times - I answered that question with "going on a date with you of course!!!")  Please don't jump through hoops trying to type things that are interesting - I'd ask him how his weekend was and use it as an opportunity to suggest -like  express interest in the activity he did and segue into maybe you two doing that if appropriate.

[Kwothe28]

What does he likes to talk about?

Sometimes its not about how interesting you are(although it always helps knowing how to tell an interesting story for example) but about making other person talk. For example you mentioned Facebook group. So maybe he likes to talk about some interest you share together on that group. 

Also, most people are "basic". Most of those people think they are all that but they are quite unremarkable. So dont worry too much about being most interesting person in the world and stuff like that. Relax and try to find some common grounds to talk and you should be fine.

Also, you should have said "I have a family thing this weekend but I am free next weekend if you want to do something". It would tell him that you are available and that he could suggest a date. 

[bluecastle]

40 minutes ago, Alex39 said:

He's mentioned maybe we can grab dinner some time. But no plans yet.

What was your response to this, out of curiosity? 

There is nothing cute or interesting about trying to be either of those things. Those things, after all, are subjective: what I find cute and interesting you may deem drab and boring, and vise versa. So it goes: the beauty and mystery of people, in microcosm. 

If dude is bantering back and forth with you, odds are greater than not that he does not find the exchanges boring. Tuck that little factoid into the back pocket, exhale, and suggest a dinner hang next time you're chatting, as one thing that collectively does get stale to most people is chitchat over social media platforms. 

[Batya33]

41 minutes ago, Kwothe28 said:

Sometimes its not about how interesting you are(although it always helps knowing how to tell an interesting story for example) but about making other person talk. For example you mentioned Facebook group. So maybe he likes to talk about some interest you share together on that group. 

Yes.  People appreciate good listeners who ask good follow up questions -they're not just responding with what they've been waiting to say.

[catfeeder]

Why not just ask him to meet for a coffee? He's a stranger, so why shoot for a full date when you don't even know if you'll share chemistry or if he's a creeper?

Public place, arrive separately, leave separately, and learn whether he views himself as relationship material, or whether he wants the dreaded 'casual'.

You're learning WHY it's important to skip trying to be a model penpal--it's awkward and useless. Meet in person and learn whether he's worth your time instead of wasting your time.

[Alex39]

I've been asking lots of questions. Trying to seem interested in him. 

 

When he mentioned about dinner. I said I'd like to and showed interest. But he never asked me. He just asked what my plans were this weekend. 

[catfeeder]

Just now, Alex39 said:

I've been asking lots of questions. Trying to seem interested in him. 

 

When he mentioned about dinner. I said I'd like to and showed interest. But he never asked me. He just asked what my plans were this weekend. 

Yes, understood, you've said all of this. You're trying to 'seem'. No need for that online.

The goal is not to try to mesmerize through typing, the goal is to grab a quick meet to check one another out. So skip the whole 'interest' strategy--that's for Jane Austen novels.

Ask if he'll meet you for a quick cup. If no, or he stalls, skip him and move onto the next one. He could just be a scammer--there are plenty on FB.

If yes, you'll spend 20 to 30 minutes to learn whether you like him as a potential date.

Don't treat online dating tools like a flirting situation--nobody knows who will like whom unless and until you meet. If you are too reserved to get that done, you'll be fluttering around on your keypad long past your fertility years.

Kidding...

Go meet the people, and plan to meet a lot of them. Most people are not our match. Allow wrong matches to pass early, and don't waste time investing and impressing prematurely.

[JoyfulCompany]

First of all, if he suggested having dinner together, asked about your availability over the weekend and you said you already have something big coming up, it's perfectly decent that you offer an alternative for coffee/lunch/dinner instead.

Second of all, I think you might be overcomplicating the situation. The facts are this person is a stranger and that you have no control over how you're being perceived. Another fact is that nobody is universally interesting, it comes down to having some compatibility/chemistry in values/interests, communication and humour. I can understand being concerned about how you're coming off if what you're looking for is an ego boost/validation. But if you're looking to get to know someone and potentially find a partner, then your focus is best to be closer to yourself - how does this person make you feel, are you interested.

The more we're trying to get out of character to impress someone, the less chance there is for an authentic connection. It will either take longer than necessary to realize you're not a match or it will be a drag to maintain the facade you've built initially (and you'll eventually be exhausted with anxiety). Not worth it.
 

7 hours ago, Batya33 said:

I answered that question with "going on a date with you of course!!!"

Batya33, I mean absolutely no disrespect and I'm sure this may work well for some, but I personally would be really put off by such answer too early on. In fact, I have been. It felt like someone made up their mind or made plans for me without checking in with me first. I could appreciate such answer later on when we've established a "routine" of meeting over the weekend or something.

Alex39, just go meet the dude briefly and relax. He might be just a brief encounter in your life or a potential for something more but in any case - enjoy the process of getting to know that and him. And be careful with that mindset what they think and what they want. You may end up in a plethora of unwanted situations. Put your needs and desires first, keep your eyes open. Good luck.

[Wiseman2]

9 hours ago, Alex39 said:

He  asked what I was doing this weekend. I mentioned I have a big family thing to go to. I was wondering if he was going to ask me out. 

You need to be able to be independent to date.  The issue is you're availably. It's interesting you didn't bother to offer another time to meet.

It seems like you are bored and lonely sometimes but are terrified of dating.

Texting is not dating. It's pointless to develop some sort of "cute and flirty" text persona if you refuse to be available because you're chronically with your family.

[Alex39]

To clarify. He said maybe we can do dinner some time. I showed interest. No plan was made. On an entirely different day, during a different conversation he didn't mention a date or dinner, he briefly asked me what my weekend plans were,with no mention of a date. 

[Wiseman2]

53 minutes ago, Alex39 said:

To clarify. He said maybe we can do dinner some time. 

To clarify, why didn't you say "that sounds great, what about sometime this week?"

[Batya33]

4 hours ago, JoyfulCompany said:

atya33, I mean absolutely no disrespect and I'm sure this may work well for some, but I personally would be really put off by such answer too early on. In fact, I have been. It felt like someone made up their mind or made plans for me without checking in with me first. I could appreciate such answer later on when we've established a "routine" of meeting over the weekend or something.

LOL - I wrote that it was in a situation where we'd been dating -or I meant to - of course I wouldn't say that to a stranger nor would I do more than ask for a first meet if the contact was through an online dating site.  When I used that line it was someone I'd gone on dates with and also known for almost 2 years previously .  It's a joke -a lighthearted flirtatious comment which is funny in the right circumstances -and that's how I said it to this guy.

There was a movie -the Flamingo Kid -with Matt Dillon -maybe before you were born?? High school I think.  He calls out to a girl at the place they hang out - "want to go to a movie this weekend?" she blushingly says "yes!!" so he calls out "OK- have a good time!!!" Not verbatim sorry -yes I saw it in the theaters.  So -yes -asking out is full of lighthearted jokes.  

And if he'd not found that funny in the situation I referenced I'd have known he was a bit too stuffy.  

[Batya33]

1 hour ago, Alex39 said:

To clarify. He said maybe we can do dinner some time. I showed interest. No plan was made. On an entirely different day, during a different conversation he didn't mention a date or dinner, he briefly asked me what my weekend plans were,with no mention of a date. 

Right because read what Catfeeder wrote.  Then read it again.  At least twice. You're acting as if this is a person you're speaking with in person where you can tell tone/energy/vibe.  It's not and -- read what Catfeeder wrote.

[Alex39]

I stopped trying so hard to be cute and started just asking him lots of questions and such. He answered them, but didn't seem interested in asking any back to me. I thought that was weird and not a good sign. I feel like I'm so terrible at this. He could have asked me out for Thursday or Friday night and he didn't. I only mentioned going to a family party saturday. So doesn't seem like he's that interested in meeting. 

[smackie9]

Tip: When a guy asks you if you are available but you are busy, always suggest another time that you are available or it will look like an excuse to get out of a date. 

[Wiseman2]

10 minutes ago, Alex39 said:

He could have asked me out for Thursday or Friday night and he didn't. 

Asking questions is boring. You did not offer a time when you are available. That's on you, not him.

[Alex39]

3 minutes ago, Wiseman2 said:

Asking questions is boring. You did not offer a time when you are available. That's on you, not him.

He didn't ask me my availability for a date. He just said "hey doing anything good this weekend" so I felt like if he was asking for a date, then I would have offered up another time

[Wiseman2]

5 minutes ago, Alex39 said:

He didn't ask me my availability for a date.  When he mentioned about dinner. I said I'd like to and showed interest. 

Are you actually interested in him?

Because if you were you would have said "That sounds great what about sometime this week?" But you didn't. All you did is say you're busy with family. Which sounds like a vague excuse/game-playing

If you want penpals, social media friends, etc., that's fine but it seems you would like a date/BF.

[catfeeder]

6 hours ago, Alex39 said:

To clarify. He said maybe we can do dinner some time. I showed interest. No plan was made. On an entirely different day, during a different conversation he didn't mention a date or dinner, he briefly asked me what my weekend plans were,with no mention of a date. 

It's okay. Stop defending, we are not attacking, we are answering.

Why not skip trying to read tea leaves, and just message him an invite to meet for a quick coffee? 

You have absolutely nothing to lose.

[lostandhurt]

I agree, time to stop this back and forth texting crap and meet in person.

"Hey ______, It is really hard to get to know someone through texting so why don't we meet for coffee"

The whole time you are chatting back and forth with this guy you are wasting time you could be talking to someone else.  Cut to the chase and see how he responds.

He could be chatting up several women at the same time and you are his plan B if plan A doesn't work out.

  This is your life so take more control of your dating life and you will feel much better about it and have less time wondering what someone is thinking or feeling because you will be sitting across from them getting to know them. 

Showing interest is not boring, asking questions about someone you are interested in is not boring and be assertive is not boring. Time to stop waiting for things to happen and make them happen...

Lost

[Batya33]

2 hours ago, Alex39 said:

I stopped trying so hard to be cute and started just asking him lots of questions and such. He answered them, but didn't seem interested in asking any back to me. I thought that was weird and not a good sign. I feel like I'm so terrible at this. He could have asked me out for Thursday or Friday night and he didn't. I only mentioned going to a family party saturday. So doesn't seem like he's that interested in meeting. 

Well no because you shut him down -why should he suggest an alternative -that was on you.  You aren't good at typing back and forth to a stranger.  Why is that a skill you want to have?  I thought you wanted to date people in person.  Sure doesn't seem that way -seems like a bunch of excuses to me including an excuse to get down on yourself.

[Wonderstruck]

The fact that you titled this post "Trying hard to be interesting and cute" says it all. People who are naturally interesting and cute don't have to try.

You make it sound like you're completely devoid of personality.

 

12 hours ago, Wiseman2 said:

Asking questions is boring.

AGREED.

So, you just started interrogating him? I despise conversations where it's just one person peppering the other with question after question. That's not a conversation. It's irritating and it IS boring.

You're right that it's a bad sign that he didn't seem interested in asking YOU any questions in return. He's not curious to learn more about you.

 

On 8/25/2022 at 10:19 PM, Alex39 said:

Trying to seem interested in him.

YIKES.

I agree with everything that Wiseman wrote - you don't actually seem genuinely interested in this guy as a person.