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I don't think I'm flirting right on 1st dates or am doing something wrong with my conversations


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Posted

I've gone on several first dates lately and haven't had any luck. I feel like only 1 of them had any personality and the other ones were like interview or more factual vs. emotional conversations. At first I thought it was just that none of them have much personality but after my last date I'm wondering if maybe there's something I need to do better.

It seems like they're all just after the basics... where you're from, what you do, your hobbies, family, etc which is all fine and good, but besides that there is no emotion, fun or laughter. For example, on the last date I mentioned a few hobbies and was telling jokes or stories about them and she's looking at me like I'm crazy. I can never seem to get my date to really start laughing or do anything that's fun where I feel like we're really connecting.

With the last woman I dated we were having a lot of fun and joking around the 1st date and I'd like to get something like that again but am just not finding that. 

Prior to my last date we were joking a bit and she seemed really playful over text, but on the date it felt like we were going into business together or something. I can be a bit shy and I'm trying my best to be more playful and open up and haven't been nervous on the dates, but am just not getting anything out of them.

Any tips for how to make a first date more like a date and less like a business meeting or simple exchange of info? I just find myself doing most of the talking.

Posted

It will be like that until you meet someone you click with. It's how it is. I like a man that talks a lot, that sees humor in life, that can elaborate during a conversation. Out of 15 men I met since this summer 3 were like this. One only wanted sex, one wanted money, 3rd one didn't have a car. 

Posted (edited)
1 hour ago, Gaeta said:

It will be like that until you meet someone you click with. It's how it is. I like a man that talks a lot, that sees humor in life, that can elaborate during a conversation. Out of 15 men I met since this summer 3 were like this. One only wanted sex, one wanted money, 3rd one didn't have a car. 

How is the “didn’t have a car” relevant?!

Edited by Killian898
Posted
2 minutes ago, Killian898 said:

How is the “didn’t have a car” relevant?!

A car is needed to come to my small city. 

Posted (edited)

Why do you have to flirt?  What does that accomplish?

She's on the date with you, that means she already has decided that it's at least *possible* that she could have sex with you.  If it were not possible you would not have gotten the date.  We do know that a few women set dates with guys that they don't see in that way, but your assumption should be that she's there in a romantic capacity.

Just relax man, get out of your head and be in the moment.  You don't have to flirt to prove that you find her sexually desirable.  Just lead the conversation by asking questions, you can get 30+ minutes easy off of asking about her favorite vacation spots or whatever crappy reality TV shows she's into.

Edited by dramafreezone
Posted

You simply didn't have chemistry with those people.  When you have chemistry with someone, it just flows naturally and you don't have to try so hard to make it work.  If it feels uncomfortable and business-like then just accept that you aren't a match with that person.  Next.

  • Like 2
Posted

Sounds pretty simple tbh , when someone just looks at you , there's nothing , they don't get ya , there's no connection.  Same when you have to work to keep things going or try too hard but nothings happening anyway , same thing. You just haven't clicked with ea other, wouldn't worry too much. Also in person with anyone later, can be totally different than a call or messaging too , basically just the same thing again.

Even if you could do with some polishing , it still won't matter anyway with the wrong personality, any joy will still be pretty short lived bc it's not real.

  • Like 1
Posted
6 hours ago, max3732 said:

I've gone on several first dates lately and haven't had any luck. I feel like only 1 of them had any personality and the other ones were like interview or more factual vs. emotional conversations. At first I thought it was just that none of them have much personality but after my last date I'm wondering if maybe there's something I need to do better.

It seems like they're all just after the basics... where you're from, what you do, your hobbies, family, etc which is all fine and good, but besides that there is no emotion, fun or laughter. For example, on the last date I mentioned a few hobbies and was telling jokes or stories about them and she's looking at me like I'm crazy. I can never seem to get my date to really start laughing or do anything that's fun where I feel like we're really connecting.

With the last woman I dated we were having a lot of fun and joking around the 1st date and I'd like to get something like that again but am just not finding that. 

Prior to my last date we were joking a bit and she seemed really playful over text, but on the date it felt like we were going into business together or something. I can be a bit shy and I'm trying my best to be more playful and open up and haven't been nervous on the dates, but am just not getting anything out of them.

Any tips for how to make a first date more like a date and less like a business meeting or simple exchange of info? I just find myself doing most of the talking.

Let’s take a step back….

 

what are common about the woman you e dated? Was there something different about the one you seemed to click with?

 

how much did you talk/ text before face to face?

  • Like 1
Posted (edited)
6 hours ago, max3732 said:

I'm trying my best to be more playful and open up and haven't been nervous on the dates, but am just not getting anything out of them.

First, one-and-done is more common than not. You're getting dates so you're doing a lot right.

Relax and be yourself. Go with the flow. It's ok to be fun and light but if women think you're acting too goofy, or full of nervous mindless chatter, they will loose interest.

Trying to hard to clown around comes off as immature, trying to hide something or not being serious. 

 It's more about being a good listener, not being goofy. Also change your stance from silliness and "do they like me enough?" to observation of "do i want to see her again?".

Edited by Wiseman2
  • Like 2
Posted

There is bound to be some element of repetition there because you are meeting a new person, perfect stranger, for the first time for the same purpose. In many ways, this is a business meeting. Your business is finding a partner. The only variable is the person sitting infront of you and your chemistry. 

Don't be too discouraged. As mentioned more often than not, first meets don't lead to anything else. You can also screen a little better and observe profiles a little more before meeting with someone. 

  • Like 2
  • Author
Posted
3 hours ago, Ami1uwant said:

Let’s take a step back….

 

what are common about the woman you e dated? Was there something different about the one you seemed to click with?

 

how much did you talk/ text before face to face?

Very interesting question.

Something all the women I've dated have had in common is they are successful in their fields and are educated.

On the first date with the woman I dated I remember we shared the same taste in movies and were talking about why X movie was better than Y and it kind of lead to some teasing, like "oh, you're one of those people who always roots for characters like Z" or something like that. It was very organic and fun.

I think we also held the same topic a little longer. Like we talked for a while about trips we've taken and went into more detail. Same thing with a woman I met recently where I really enjoyed the conversation and if not for having different views on some key issues I would be happy to keep talking with her.

One of the recent dates I posted about here afterwards and she was basically interviewing me and I'd start to setup a story and then she'd ask about a different topic. Like she'd ask "what kinds of restaurants do you like" and I'd answer and be ready to talk about a place and an experience there and then she'd say "do you have any siblings?".

With 2 of the other recent dates I was talking and going into detail, but they never really did. There wasn't any back and forth with the conversation either. For example, on my date this week she said "my mom would get mad at me growing up since I could be a handful". I asked what kinds of things she'd get into and her response was "typical teenage girl stuff". I was kind of hoping for a story or something to build on. When she asked me about a hobby I'd get really excited and passionate explaining why I like it and just get this blank stare back.

I'm not clowning around like making snakes with the straw wrappers or anything like that. It just feels like the whole date is so serious and fact based and I don't know if that builds attraction. Even though it is like a business meeting isn't there more I can do to spark chemistry or romance? Maybe ask better questions?

Posted
37 minutes ago, max3732 said:

Very interesting question.

Something all the women I've dated have had in common is they are successful in their fields and are educated.

On the first date with the woman I dated I remember we shared the same taste in movies and were talking about why X movie was better than Y and it kind of lead to some teasing, like "oh, you're one of those people who always roots for characters like Z" or something like that. It was very organic and fun.

I think we also held the same topic a little longer. Like we talked for a while about trips we've taken and went into more detail. Same thing with a woman I met recently where I really enjoyed the conversation and if not for having different views on some key issues I would be happy to keep talking with her.

One of the recent dates I posted about here afterwards and she was basically interviewing me and I'd start to setup a story and then she'd ask about a different topic. Like she'd ask "what kinds of restaurants do you like" and I'd answer and be ready to talk about a place and an experience there and then she'd say "do you have any siblings?".

With 2 of the other recent dates I was talking and going into detail, but they never really did. There wasn't any back and forth with the conversation either. For example, on my date this week she said "my mom would get mad at me growing up since I could be a handful". I asked what kinds of things she'd get into and her response was "typical teenage girl stuff". I was kind of hoping for a story or something to build on. When she asked me about a hobby I'd get really excited and passionate explaining why I like it and just get this blank stare back.

I'm not clowning around like making snakes with the straw wrappers or anything like that. It just feels like the whole date is so serious and fact based and I don't know if that builds attraction. Even though it is like a business meeting isn't there more I can do to spark chemistry or romance? Maybe ask better questions?


 

I don’t like when the convo becomes more of a Q&A but instead is a good conversation.  

how are you measuring intelligence?  By career choice or degree level?

 

Im looking at if they had trends like being a similar type or style and maybe you don’t mensch with them.  I don’t care for women who come off as two artsy or appear to be two into the latest fashion.

 

you didn’t answer some of my questions I asked.  If you talk too much before the date, you might run out of what to talk to.

 

there could be something youare doing when you eat that can be a turn off either in things you order or comments you make on your food dtyle and choices or you chew with mouth open.

 

have you thought about doing something different like an activity date instead of it being meal driven.

do you have a sister or female friend that could see your mannerisms or behavior. Maybe watch from a distance on your date?

 

 

 

 

 

 

 

  • Author
Posted
32 minutes ago, Ami1uwant said:


 

I don’t like when the convo becomes more of a Q&A but instead is a good conversation.  

how are you measuring intelligence?  By career choice or degree level?

 

Im looking at if they had trends like being a similar type or style and maybe you don’t mensch with them.  I don’t care for women who come off as two artsy or appear to be two into the latest fashion.

 

you didn’t answer some of my questions I asked.  If you talk too much before the date, you might run out of what to talk to.

 

there could be something youare doing when you eat that can be a turn off either in things you order or comments you make on your food dtyle and choices or you chew with mouth open.

 

have you thought about doing something different like an activity date instead of it being meal driven.

do you have a sister or female friend that could see your mannerisms or behavior. Maybe watch from a distance on your date?

 

 

 

 

 

 

 

I'm measuring intelligence by career choice/results. All of them are successful at difficult jobs that require a great deal of training.

I also don't care for women who are too artsy or too into always having the latest fashion. Their styles have been rather different. Also before the date I've talked quite with them for about a week. Just some basic screening.

With the one I dated long term I texted and talked to on the phone a few times before meeting.

Usually I will ask them what kind of food they like and talk about a lot of items on the menu and share my tastes. If I chewed with my mouth open I think my friends would tell me, but it is possible I do something else on a date I don't normally do.

One problem I've had in the past is when I get really nervous on a date I'd started blinking uncontrollably. I did feel that in one of these dates but not the other ones. 

No sister or female friend that would observe from a distance. I have 1 female friend near my age that is single who I've talked to about what happens on my dates. I don't think she'd observe from another table.

I've done activity dates before and am open to that. 

Posted
5 hours ago, Wiseman2 said:

 It's more about being a good listener, not being goofy. Also change your stance from silliness and "do they like me enough?" to observation of "do i want to see her again?".

The issue is he says they're asking him questions.   That needs to flip OP.  You ask the questions, you control the direction of the conversation.  And all people want to do is talk about themselves, so let them. 

OP, your dates don't actually want to talk about that mundane crap (the basics as you say).  They're only filling the time because you're not leading a good conversation.  Get them on a topic that they enjoy.

  • Like 1
Posted
2 hours ago, max3732 said:

...

I'm not clowning around like making snakes with the straw wrappers or anything like that. It just feels like the whole date is so serious and fact based and I don't know if that builds attraction. Even though it is like a business meeting isn't there more I can do to spark chemistry or romance? Maybe ask better questions?

Doesn't sound like you are doing anything fundamentally "wrong" it just takes two to tango.  I'm with you on not liking the "job interview.," it takes all my will power not to mess with that.  As in, if they ask me what I do for a living, saying something like "As little as possible." :)    

All I can suggest on sparking chemistry and romance is to be you, as it is you that you want them to like.  Being passionate about a hobby is generally not bad, unless they are like "ewww" on the hobby.  You really can't predict that, so be you.   Same with attaching a story to things, that sounds great.    Long story short (pun intended) sounds like them and not you.  Then it may be a question of the pond you are fishing in, or your picker.

  • Like 1
Posted (edited)
5 hours ago, max3732 said:

Very interesting question.

Something all the women I've dated have had in common is they are successful in their fields and are educated.

On the first date with the woman I dated I remember we shared the same taste in movies and were talking about why X movie was better than Y and it kind of lead to some teasing, like "oh, you're one of those people who always roots for characters like Z" or something like that. It was very organic and fun.

I think we also held the same topic a little longer. Like we talked for a while about trips we've taken and went into more detail. Same thing with a woman I met recently where I really enjoyed the conversation and if not for having different views on some key issues I would be happy to keep talking with her.

One of the recent dates I posted about here afterwards and she was basically interviewing me and I'd start to setup a story and then she'd ask about a different topic. Like she'd ask "what kinds of restaurants do you like" and I'd answer and be ready to talk about a place and an experience there and then she'd say "do you have any siblings?".

With 2 of the other recent dates I was talking and going into detail, but they never really did. There wasn't any back and forth with the conversation either. For example, on my date this week she said "my mom would get mad at me growing up since I could be a handful". I asked what kinds of things she'd get into and her response was "typical teenage girl stuff". I was kind of hoping for a story or something to build on. When she asked me about a hobby I'd get really excited and passionate explaining why I like it and just get this blank stare back.

I'm not clowning around like making snakes with the straw wrappers or anything like that. It just feels like the whole date is so serious and fact based and I don't know if that builds attraction. Even though it is like a business meeting isn't there more I can do to spark chemistry or romance? Maybe ask better questions?

As l said , wouldn't matter. There's obviously been zero of anything much with any of them so far none of them would turn into anything anyway. lt;s just squeezing blood out of a dead stone.

When you get along everything you talked about here is out the window, it just is, happens, natural.

Edited by chillii
Posted

Common Mistake men make is we talk too much. Say as little as possible. be mysterious. see how that works 

  • Like 1
Posted
7 hours ago, max3732 said:

Very interesting question.

Something all the women I've dated have had in common is they are successful in their fields and are educated.

On the first date with the woman I dated I remember we shared the same taste in movies and were talking about why X movie was better than Y and it kind of lead to some teasing, like "oh, you're one of those people who always roots for characters like Z" or something like that. It was very organic and fun.

I think we also held the same topic a little longer. Like we talked for a while about trips we've taken and went into more detail. Same thing with a woman I met recently where I really enjoyed the conversation and if not for having different views on some key issues I would be happy to keep talking with her.

One of the recent dates I posted about here afterwards and she was basically interviewing me and I'd start to setup a story and then she'd ask about a different topic. Like she'd ask "what kinds of restaurants do you like" and I'd answer and be ready to talk about a place and an experience there and then she'd say "do you have any siblings?".

With 2 of the other recent dates I was talking and going into detail, but they never really did. There wasn't any back and forth with the conversation either. For example, on my date this week she said "my mom would get mad at me growing up since I could be a handful". I asked what kinds of things she'd get into and her response was "typical teenage girl stuff". I was kind of hoping for a story or something to build on. When she asked me about a hobby I'd get really excited and passionate explaining why I like it and just get this blank stare back.

I'm not clowning around like making snakes with the straw wrappers or anything like that. It just feels like the whole date is so serious and fact based and I don't know if that builds attraction. Even though it is like a business meeting isn't there more I can do to spark chemistry or romance? Maybe ask better questions?

You may be too longwinded or verbose. If someone asks you what your favourite restaurants are, name a couple off the top of your head or mention a couple that you enjoyed and went to recently. Return the same question or ask what her favourite foods are. Stories get irritating and stale if you are taking a longwinded approach to a direct question that only requires a simple answer. You'll build rapport and chemistry over time. It's not something that can be rushed, that mutual feeling of getting or understanding one another. 

It sounds like you only had two awkward dates and the others prior were fine. 

Don't overreact or get too upset over this. It happens. Let it roll off your back and enjoy your time with that person. Some people are naturally or by nature serious or direct. If they are incompatible with you, that's perfectly fine. Move on to find someone who likes telling longer stories like you do.

  • Like 1
Posted (edited)
8 hours ago, max3732 said:

  I don't know if that builds attraction. 

That's not your job on a date. It's a horsechips term from pickup artist sites. So is being cocky and trying to make her laugh.

Building attraction is a myth. Either they're attracted or they're not. Stop focusing on that.

So what if she asks questions about your life, interests etc? That's what first meetings are for.

 

Edited by Wiseman2
  • Like 3
Posted
1 hour ago, ajequals said:

Say as little as possible. be mysterious. see how that works 

You know how you complained about women who can’t have a decent conversation?  I think someone gave them this same advice and they listened to it.   

Nobody wants a date who can’t hold up their end of a conversation.  And if those women you’ve dated can’t hold up a conversation, it’s not your fault.  They are clearly single for a very good reason. 

 

  • Like 2
Posted

Your theory of dating is wrong.

The vast majority of people you meet are people you will NOT have a connection with.

Online dating is just mildly this side of totally random. In real life we get to pre-screen a first date much better (meeting someone through a friend or at a party) before meeting them on a date.  Online dating, despite the list of hobbies, despite the photos, hasn't caught up with real life in any way. I'm sure that there are algorithms that over time will make things better, but for now, you're NOT going to feel connected with most people. That's OK. 

For online dating, you have to think of meeting 30, 40, 50 people. See it as a project for a year or more. So fix your theory here--your hit rate is going to be very low.

Next, you flirt as a result of connection, not the other way around. When you connect with someone, you will feel powerful energy and that energy goes to the other person and they send energy back to  you. Flirting doesn't create the spark. Flirting emerges as a result of spark. Now, if you want to just pick up people for sex, sure you can focus on flirting because you won't really be learning about the other person or screening for people you have long-term potential with.

Next, dating requires getting in touch with your body and gut. The questions and banter feel like interviews--that means your gut is not feeling anything exciting. Means there is no chemistry. That's reality and truth there--not evidence of poor flirting skills.  So relax on these days and just talk about anything you want. 

Now, there is a way certain people block flirting energy. So you may need a bit of a fix here. If something pops whe you meet the person, like you think they are really well dressed or funny or you like their voice or like their thinking, you want to say that! But I don't sense that you've felt strong positive reactions. It's just that when you do feeling something strong, you gotta respond and react and indicate what you feel great about. "Wow, love the way you think and talk." Again, this tends to happen naturally. If someone is really funny,  you laugh and that indicates interest.

You have to get your numbers up. Meeting 50 people online is probably equivalent to meeting five or ten people through real-life situations and in real life, it's easy to meet ten people you have absolutely no interest in. And in real life there are plenty of times you are actually are on a first meet (equivalent to these meetings you've had). You talk to someone at work ... or some other situation. Most of those meetings do not lead to romance. 

One tip I will offer. Since the online dating algorithms are so terrible, I say meet with almost anyone who looks to have some potential (within some limits). And don't trust photos--good or bad. Someone can look different than photo and combined with a personality trait that doesn't come through in the online profile, you could find them very attractive. If the profile is interesting, go meet the person. Don't let looks disqualify you because likely you are projecting all kinds of qualities onto the people you think look good. And photos don't capture a person's real-life energy and charisma. 

 

 

  • Like 3
Posted

There's "having a good time" and then there's "assessing whether a person is a good potential LT mate". Both important, but maybe try to steer the conversation and indeed the whole occasion back toward having a good time. There IS such a thing as ST flings, and they can be quite fun, etc...

It's also possible the women you happened to be with simply don't have particularly good personalities. It's 3 out of like 150+M or so women (assuming you're in the US), so a small very sample.

Posted
18 hours ago, max3732 said:

I'm measuring intelligence by career choice/results. All of them are successful at difficult jobs that require a great deal of training.

I also don't care for women who are too artsy or too into always having the latest fashion. Their styles have been rather different. Also before the date I've talked quite with them for about a week. Just some basic screening.

With the one I dated long term I texted and talked to on the phone a few times before meeting.

Usually I will ask them what kind of food they like and talk about a lot of items on the menu and share my tastes. If I chewed with my mouth open I think my friends would tell me, but it is possible I do something else on a date I don't normally do.

One problem I've had in the past is when I get really nervous on a date I'd started blinking uncontrollably. I did feel that in one of these dates but not the other ones. 

No sister or female friend that would observe from a distance. I have 1 female friend near my age that is single who I've talked to about what happens on my dates. I don't think she'd observe from another table.

I've done activity dates before and am open to that. 


 

I disagree with what wiseman said above when it comes to online dating.

 

Instant attraction is not the norm.  
 

pre online many times there wasn’t this fantasy instant attraction.  They did a slow build up where they first met someone then got to know them when they saw each other again and it was a slow build up before a date happened.

 

online dating is different in that you communicate prior to meeting so psychologically there is a different type of expectation.  With some attraction doesn’t happen in time but takes a few dates.

 

if you have decent convo on first meet and their wasn’t any big red flags…meet again.

 

part of the problem is unrealistic expectations these women have on a first date of instant attraction.

 

you can easily screen matches if they list degree level.  Having a degree and intelligence is different.  Some might be book/ skill smart but other areas they could be rather naive or clueless.

 

if you are talking to much it coukd turn them off.  Are you skiing questions to them?  My successful dates fir a first meet was when there was good conversation flow. What I learned is to not talk to much before the face to face so you have stuff to talk about.

 

sure nerves can affect things.  Sometimes it could make your face say one thing that isn’t how to feel inside  your eyes could be doing something like stare of lack of contact or you talking at their breasts.

 

another issue…are you trying to date someone out of your league on beauty?  Some women might dismiss you because they think you are too short or you aren’t built like they like.  These you can’t change.

 

how are you in interacting with women you aren’t dating?

 

 

 

 

  • Author
Posted
9 hours ago, Lotsgoingon said:

Now, there is a way certain people block flirting energy. So you may need a bit of a fix here. If something pops whe you meet the person, like you think they are really well dressed or funny or you like their voice or like their thinking, you want to say that! But I don't sense that you've felt strong positive reactions. It's just that when you do feeling something strong, you gotta respond and react and indicate what you feel great about. "Wow, love the way you think and talk." Again, this tends to happen naturally. If someone is really funny,  you laugh and that indicates interest.

You have to get your numbers up. Meeting 50 people online is probably equivalent to meeting five or ten people through real-life situations and in real life, it's easy to meet ten people you have absolutely no interest in. And in real life there are plenty of times you are actually are on a first meet (equivalent to these meetings you've had). You talk to someone at work ... or some other situation. Most of those meetings do not lead to romance. 

One tip I will offer. Since the online dating algorithms are so terrible, I say meet with almost anyone who looks to have some potential (within some limits). And don't trust photos--good or bad. Someone can look different than photo and combined with a personality trait that doesn't come through in the online profile, you could find them very attractive. If the profile is interesting, go meet the person. Don't let looks disqualify you because likely you are projecting all kinds of qualities onto the people you think look good. And photos don't capture a person's real-life energy and charisma. 

I didn't really think about it like that but you're right about not really knowing much about these people and not having much in the way of a "pre screen" as I would in real life.

Usually I've been afraid of giving a woman a compliment since I don't want to put them on a pedestal or just have them think I'm interested in her looks. To give an example from my last date of a compliment I did give though. She was wearing a stunning green dress. I told her that she looks amazing in that dress and I wish I'd worn my green shirt so we'd match or something like that. It just popped in my head. Is that ok? The other thing with the dress was it showed a lot of cleavage and I was actively trying to avoid staring at it. Although I also complimented her on her necklace and got a story from her about it.

6 hours ago, mark clemson said:

There's "having a good time" and then there's "assessing whether a person is a good potential LT mate". Both important, but maybe try to steer the conversation and indeed the whole occasion back toward having a good time. There IS such a thing as ST flings, and they can be quite fun, etc...

What I'm looking for is someone to marry and don't want to be with someone just because she's pretty, successful in her career and smart if she has a personality I don't enjoy. 

 

4 hours ago, Ami1uwant said:

if you are talking to much it coukd turn them off.  Are you skiing questions to them?  My successful dates fir a first meet was when there was good conversation flow. What I learned is to not talk to much before the face to face so you have stuff to talk about.

I am asking them questions but I'm wondering if I'm asking the wrong questions. Like maybe mine are too formal and not fun or ones that would help to get to know who she is beyond the superficial stuff and get me to see the personal (vs professional) side of her.

4 hours ago, Ami1uwant said:

another issue…are you trying to date someone out of your league on beauty?  Some women might dismiss you because they think you are too short or you aren’t built like they like.  These you can’t change.

 

how are you in interacting with women you aren’t dating?

I've been taller than everyone I've gone out with by at least 3 inches. I think I'm attractive, but then again I might be somewhat biased. I also work out regularly and am in pretty good shape, but I'm not a bodybuilder or fashion model. The only thing I know I've done is the past is that stupid rapid blinking when I get nervous and I don't know how to fix that.

With women I'm not dating there's really only 1 around my age who is single and we have a rather odd situation. We are working on our sports game together and share our dating and professional experiences.  At 1 point I considered dating her, but don't think she's right for me. However she's gone back and forth with being like a regular friend and almost flirty. One thing she's said is she wants a guy who will put her in her place, which I'm guessing she doesn't think I'd do.

Aside from her the only women I interact with are family members, ones at work or just when I go out to run errands and such.

Posted

You don't want to just compliment the dress or the jewelry. Well let me back up. You give the compliment because you STRONGLY like the dress and the color. 

You say you like the dress in a way that means "I like the way you look." You're not putting someone on a pedestal by giving them a genuine compliment. They might still be idiots who you don't like for ten other reasons. You give the compliment because you strongly feel it. Doesn't mean you think they are smart or interesting, or creative or clever or funny or a reliable or kind or that they share your key values and perspectives on the world or anything else. You with me? So lose the fear there.

Saying you had a matching green shirt ... no, that's taking the energy away from focusing on the other person. You undermine yourself with that. Step up and say what you like about the other person. Period!

If you're having a great time or it's a great conversation, say that. Again, you probably are not having great conversations, so you don't want to say anything that isn't true.

Just keep meeting people. 

BTW: what kinds of questions are you asking? You say you worry that your questions are too formal. 

 

 

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