I'm 30 years old and I never really dated. I haven't had weight loss surgery, I'm trying to lose weight on my own without surgery and doing well. I've went from 470 to 430 in about two months. I'm not ready to meet women yet as I wanted to be under 300 before I do that. I'm not sure how to do it. I've always avoided socializing but I feel a big reason I gained so much weight was due to loneliness. I created an online account but didn't add any information or pictures, just wanted to look. I see a lot of women I am interested in but I have no idea how to introduce myself or what I should say. If it progresses to a date I have no idea what to do or where to go on a date. I don't know when I should kiss a woman or request a second date. I feel like I shouldn't need to be figuring this out at 30. This seems like something I should have learned in high school. Is there like a tutorial for this? I feel like it just gets harder to find someone after 30 and throw in the fact I have virtually no dating experience.

3 hours ago, sgc said:

I updated the pics in my profile and that seemed to generate some activity. Been having a nice back and forth with another woman. When should I escalate this to an in person meeting? What should the first date or meeting be?

Well that's good. How long have you been talking to her. My suggestion is wait about 1 week after talking just to make sure that the chemistry is really there.

Well that's good. How long have you been talking to her. My suggestion is wait about 1 week after talking just to make sure that the chemistry is really there.

It has only been a day but several messages. She was replying almost instantly. The problem once again is that she isn't asking me questions. It seems like I'm keeping the conversation going. She emailed me initially saying she would like to chat. I sort of tested her by replying and not asking her anything. She replied and it was short and with no question. I seem to run into this with the few who do show interest.

Open ended questions good sir. Make her speak to you. If she is unable to tell you about herself in an open ended question she is either not interested or has the personality of a rock. I would review her profile, look for the items that show her interests. If you see a common interest ask about it. Example, if she says she likes hiking and in the off chance you may also or you may be curious about it. "Hey there (Insert name of romantic interests here) I notice on your profile you said you enjoyed hiking. I have been interested in finding cool places to hike also. Tell me about your experiences." No need to use verbatim but notice, she can't give you a yes or no answer without sounding like a complete dolt who is being evasive, she has to fork over some information which can then lead to more questions ANNNND hopefully get her to engage you with questions since you have shown interest in something she likes.

Open ended questions good sir. Make her speak to you. If she is unable to tell you about herself in an open ended question she is either not interested or has the personality of a rock. I would review her profile, look for the items that show her interests. If you see a common interest ask about it. Example, if she says she likes hiking and in the off chance you may also or you may be curious about it. "Hey there (Insert name of romantic interests here) I notice on your profile you said you enjoyed hiking. I have been interested in finding cool places to hike also. Tell me about your experiences." No need to use verbatim but notice, she can't give you a yes or no answer without sounding like a complete dolt who is being evasive, she has to fork over some information which can then lead to more questions ANNNND hopefully get her to engage you with questions since you have shown interest in something she likes.

I have done that and she has responded with somewhat detailed answers but she doesn't ask me anything. She had talked about a trip she had taken so I figured I would test her and said that sounded like fun, I will have to try that sometime. Didn't ask her a question. She responded right away and basically said it was but didn't ask me anything. Not sure where this is going. She emailed me first and responds right away to my emails but I feel I'm keeping the conversation going.

19 minutes ago, sgc said:

I have done that and she has responded with somewhat detailed answers but she doesn't ask me anything. She had talked about a trip she had taken so I figured I would test her and said that sounded like fun, I will have to try that sometime. Didn't ask her a question. She responded right away and basically said it was but didn't ask me anything. Not sure where this is going. She emailed me first and responds right away to my emails but I feel I'm keeping the conversation going.

Pros and cons to this:

Pros -

SHE initiated. If she started this then we must assume there is interest. This is good.

She responds quickly. She is wanting more communication from you, again this is good.

Cons-

Lacks follow up on questions

Your feeling like you sustain this conversation

This is not as bad a deal as you may be feeling. You may have to get creative and start volunteering somethings about yourself. "Tootin your own horn" if you will. Keep digging through her profile and pay attention to the "little things" she says and expresses interest in. Not sure what dating site you are on, but if she gave some descriptors on the kind of man she wants to find. Work that into a conversation piece. You may have to work a little harder at this than you expected, and you may have to volunteer more of yourself rather than waiting on her to question you. That's ok, find that common interest(s) and run with it. Relay a story on something you experienced based on a common interest she has with you. Avoid negative past experiences with other women at all costs - no one likes to hear about ex-anythings and the one sided stories that usually accompanying them

Pros and cons to this:
Pros -
SHE initiated. If she started this then we must assume there is interest. This is good.
She responds quickly. She is wanting more communication from you, again this is good.
Cons-
Lacks follow up on questions
Your feeling like you sustain this conversation
This is not as bad a deal as you may be feeling. You may have to get creative and start volunteering somethings about yourself. "Tootin your own horn" if you will. Keep digging through her profile and pay attention to the "little things" she says and expresses interest in. Not sure what dating site you are on, but if she gave some descriptors on the kind of man she wants to find. Work that into a conversation piece. You may have to work a little harder at this than you expected, and you may have to volunteer more of yourself rather than waiting on her to question you. That's ok, find that common interest(s) and run with it. Relay a story on something you experienced based on a common interest she has with you. Avoid negative past experiences with other women at all costs - no one likes to hear about ex-anythings and the one sided stories that usually accompanying them

I have volunteered some information on myself. I'm just hoping her lack of questions isn't a lack of interest.

14 minutes ago, sgc said:

I have volunteered some information on myself. I'm just hoping her lack of questions isn't a lack of interest.

For now at least, I am gonna say no I don't think it is. THe overwhelming evidence in the fact that she initiated and responds quickly is an indicator of interest. Stay cool, stay positive, and be yourself. As @thejeweledsleeve advised invest some time in communicating then in a week if you feel a meet is warranted, suggest something to do that's an interest to both of you and preferably that doesn't revolve around food. Consider maybe going bowling, shooting pool, or to bring out the kid in each of you maybe some go-kart racing if they have that in your area and weather permits.

For now, focus on information exchange even if you have to do most of the legwork. She may be one of those who feels she should not have to do any pursuing and if you are truly interested you will do the work, they are tough nuts to crack but its a good exercise for your personality to keep it elevated. When it comes time for meet and greet we can go over ideas on things to do, but right now communication is king and you need to focus on advertising yourself as the great catch you believe yourself to be.

Really struggling with this communication thing. I threw a test at the one woman and didn't ask a question. She never returned my message so that faded. Another one liked me and I sent an email and she replied but again with no question and no response. I sent an email to another one who actually responded (I'm 2 for about 170) and she just said "Hey, how are you?" didn't even answer what I asked and makes me wonder if she even read my email. Why are women approaching me if they don't want to talk to me? Is this some sort of game?

17 hours ago, sgc said:

Really struggling with this communication thing. I threw a test at the one woman and didn't ask a question. She never returned my message so that faded. Another one liked me and I sent an email and she replied but again with no question and no response. I sent an email to another one who actually responded (I'm 2 for about 170) and she just said "Hey, how are you?" didn't even answer what I asked and makes me wonder if she even read my email. Why are women approaching me if they don't want to talk to me? Is this some sort of game?

Let's slow down for a sec and take a breath. Let me pick this apart and offer some friendly encouragement/advise, free of charge so take it as you see fit.

"I threw a test at the one woman.." can be perceived by others as you playing a game, the very thing you are expressing frustration over. I would encourage you to scrap all notions of "testing" anyone.

Just be you.

Ask your questions. Make them thought provoking "open ended questions" meaning they can't give you a yes or no answer and if they don't address what you are asking, then delete as they obviously do not see it as important enough. That being said, make sure you are not asking questions outside the scope of the time you are getting to know someone. Meaning, don't get too personal too quick.

What dating site are you using?

If you search through their interests, those are safe topics to question as they made them known to everyone. If they enjoy travel ask them about their favorite destinations, ask them what places they still want to visit and why it appeals to them etc.

Its ok to focus on them for awhile but I do have compassion for your cause if they don't reciprocate communication and ask somethings about you after awhile. Patience will be key here. By the third or fourth email...and I am being generous, if they haven't wanted to know something deeper about you and your interests, I am gonna say not worth the effort, especially after you have sent over a number of questions about interests they've expressed on their profiles.

Lastly, this is all based on one side of the story. There are 3 sides to every story, yours, theirs and the truth. I can't see your profile, I can't see your email exchanges so I am taking you at face value. However only you can honestly answer if you are being fair to these women or whether or not you are looking to sabotage any progress you are making out of fear of eventual rejection...yes there are men and women out there who do just that. Just be yourself, show interest in their interests, ask open ended questions and move along if they are not equally sharing. It is a numbers game, and online dating hides many pitfalls as people can be whoever they want you to believe they are thanks to the anonymity of the internet. At the end of the day, maybe internet dating isn't a good route for you and that is ok also. You may fare better getting out and finding activities where you can socialize and let your personality show who you are if your words in emails aren't getting it done. Just some things to consider.

When I say test, I replied to her message but didn't ask a question. We had exchanged 10 messages each and she hadn't asked me anything. If I'm expected to keep the conversation going, that's not going to work for me. I asked open ended questions and it did lead to talking about her travels but she was just answering my questions. She didn't have a lot of details on her profile. This was through Match. It's just weird that she initiates conversation with me and then doesn't seem interested in knowing me.

So hey how are you girl emailed me back. I had replied to her email and said I was doing well and through her a softball question asking what she does for fun. That was Wednesday. Not holding out a lot of hope but she did answer and ask me what I do so I responded and started asking more thoughtful questions. I was surprised she even responded to me in the first place. She seemed out of my league. She runs marathons and seems like she will be more fit than myself which can be intimidating. I'm really not sure if she truly is interested or not. Guess I'll find out.

She emailed me back right away this time. Didn't ask me a question though. I'll have to try to dig deeper.

16 hours ago, sgc said:

She emailed me back right away this time. Didn't ask me a question though. I'll have to try to dig deeper.

Well well well...the fruits of your labor are starting to blossom...no guarantee this will pan out, but like I said, some ladies are tough nuts to crack and extra effort is required. Keep it low key, don't get too personal too quickly and most importantly, have fun with it. You're meeting someone new with potential. And for the record, I do not believe in the phrase "out of my league". Usually when others make that comment to me, " Don't you think she's out of your league?" My response is simple, "Yes but she's seems like she has a good personality so I thought I'd give her a chance." (translation - I am allowing her up into my league) No one is ever too good for you if you feel and believe that you deserve the best life has to offer because of who you are and what you have to give to them. Shine, and make them wonder what you've got as they look inward from the outside of your life. Enjoy your conversations and best wishes.

Hi sgc,

You began this post nearly 2 years ago. Your requests for advice haven't changed in those 2 years even though you've been given very similar advice many many times. If you keep doing the same thing you are going to continue getting the same results and that is what's happening here. Your stories and answers are repeats of what what said months, and now years, earlier. People who have commented earlier have quit commenting. New people join this forum and they begin offering similar advice that you've already received so this post keeps going. I gave you my suggestions but they were turned down so I quit commenting. At some point you have to step up to the plate and take action. If you have social anxiety then work on that with a therapist before you begin dating. Sometimes I wonder if this is just a game you are playing on all of us who take this forum seriously. SO, if your posts are serious I suggest you go to counseling to work your own issues out. Social Anxiety can't be cured in a forum. I wish you the best.

1 hour ago, ShelbyMoore said:

Hi sgc,

You began this post nearly 2 years ago. Your requests for advice haven't changed in those 2 years even though you've been given very similar advice many many times. If you keep doing the same thing you are going to continue getting the same results and that is what's happening here. Your stories and answers are repeats of what what said months, and now years, earlier. People who have commented earlier have quit commenting. New people join this forum and they begin offering similar advice that you've already received so this post keeps going. I gave you my suggestions but they were turned down so I quit commenting. At some point you have to step up to the plate and take action. If you have social anxiety then work on that with a therapist before you begin dating. Sometimes I wonder if this is just a game you are playing on all of us who take this forum seriously. SO, if your posts are serious I suggest you go to counseling to work your own issues out. Social Anxiety can't be cured in a forum. I wish you the best.

If that is the case, then yes there may be a bit of social anxiety; and if so, dating is ill advised until some counseling can be obtained to help sort out whatever impediments may be present which can only help him. Dating with these kinds of unresolved issues will only result in difficulties where there need not be any.