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.

@clc9 now thinking about it, I do agree. I have never dated anyone I worked with. Besides, could it be that you have not connected with her in the way you would have hoped?

I say try the dating apps. If you do not fear rejection, I am sure you will be able to find a nice female.

As far as not being able to tell someone you aren't into them can be difficult but stringing someone along can be emotional damaging too.

The reasons I considered dating a co-worker is that we both work from home so we never actually see each other and we both do different jobs and don't need to communicate with each other to do our jobs. My concern is if it doesn't end well, is she the type that will get mad and try to sabotage me at work?

I did go on eHarmony and liked it but didn't put much effort in it. I kind of just wanted to poke around. I didn't upload any pics or anything. I like how I don't have to come up with clever pick up lines. I was also matched up with this same woman at work a year ago. The sad part is, I don't have people to take pictures of me so I have to bust out my tripod one of these days and get some updated pics.

There is nothing sad about that. Tripods are awesome. Listen, if you feel she maybe the woman for you then go for it.

You feelings of whether she would be Vindictive is a valid point and concern. That's mainly why people don't like dating co-workers. I mean since you guys work remotely, you it may work out

I seem to over analyze things. I'm plotting out how to create an online profile and I want good pictures. I want the pictures to make it seem like I'm with people and natural and not posing for a picture.

I don't think she is the type to be vindictive but I don't know. Maybe our paths will cross again on eHarmony. Last time I didn't have any pictures or filled out my profile so she likely didn't know it was me. There is also a company sponsored even coming up in a couple weeks that I'm pretty sure she will be at. Problem is, there could be 20-30 people and I'm not good in crowds and mingling. There's also going to be bowling and I haven't bowled in years because I was too big and it would hurt my back and give me muscle spasms. Even when I did bowl, I wasn't particularly good at it. Not sure If I'm going to go or not.

I decided to go this work outing next Saturday that I know she will be at. A big part of why I decided to go was that she will be there but another part is that this is something I would have never done before big or thin. There will probably be at least a dozen people there and I can't just avoid socializing all the time. It will be good practice since it's people I know vs trying to engage with new people. Maybe I can get her alone for a minute and talk as well. In any even it will be good practice.

@sgc how did that event go on Saturday? You never gave us an update. Waiting patiently.

It's actually tomorrow. I did get a look at the list of who is attending and she will be there but so will 25 other people. I'm not good in big crowds even though I know most of the people who will be there. I seem to have an odd personality. I'm so uncomfortable approaching people, but yet I'm a very good public speaker. I will see how this goes. Have been agonizing over what to wear and whether I should shave or not or what time I should arrive. I always over analyze these things. I'm thinking after I will set up my online dating profile. My goal weight was 250 but now I'm done into the 230's so maybe I'll settle around 200. I've been writing a profile in Word as I get ideas. Also started researching what types of pictures to use. Going to get out my tripod and stage pictures like I have an active life.

I have developed a plan. I imagine that with 26 people, they will start splintering off into smaller groups so I will gravitate to whatever group she is with. From there I will kind of gauge the situation. This thing ends around 10:30. Since it's a work thing, there's no alcohol. I'll assess the situation and see if an opportunity arises and ask her to go for a drink or something after. This is not something I have done before so it remains to be seen if I can follow through on it.

4 hours ago, sgc said:

It's actually tomorrow. I did get a look at the list of who is attending and she will be there but so will 25 other people. I'm not good in big crowds even though I know most of the people who will be there. I seem to have an odd personality. I'm so uncomfortable approaching people, but yet I'm a very good public speaker. I will see how this goes. Have been agonizing over what to wear and whether I should shave or not or what time I should arrive. I always over analyze these things. I'm thinking after I will set up my online dating profile. My goal weight was 250 but now I'm done into the 230's so maybe I'll settle around 200. I've been writing a profile in Word as I get ideas. Also started researching what types of pictures to use. Going to get out my tripod and stage pictures like I have an active life.

Well good luck for tomorrow. I hope you have a good time. Also mingle with other groups. You never know whom you might meet and get along with. You may even start a Bromance, which every guy needs.

It is okay. We all over analyze things from time to time. Its because we want to impress people. Everyone wants to be liked.

It went basically how I suspected it would go. I faded into the background. I talked to her some. Just don't think the fit is there anymore. She's more of a going out and being in bigger crowds and that's just not who I am. She knows a lot more people at work so if this didn't work out, it could be bad for me. I've been working on building an online dating profile. I will start that here soon. This event may not have been a good idea because it plays to all my weaknesses. I need to be more one on one.

@sgc though the event did not go well, you cannot slip into the background. When we have weaknesses, we work on them to make them stronger. Large groups and being social may not be your thing but you also have to remember that you hid from the world, we all did at some point. You are still thinking like the old you. The point was to experience life to the fullest and not to continue living with that mindset. We do not know who we are and what we like until we have truly experienced those things.

I am a very social person, it is hard for me to fade into the background and not steal the attention. For instance, I work for a pretty nice size company however, everyone in the parent company knows who I am and says hi to me all the time. I have never been to a company event (my free time is that...my free time) and yet people know me. I suck at one on ones with people though. I can't carry a full conversation because being a Gemini, I get bored easily and will seek out other conversations. With that being said, you thrive with one on one's and I thrive in groups. I have put myself in enough situations in which I learned how to carry one one one conversations for longer than 3 minutes (I can go 5 minutes lol). The goal is to do the things that make uncomfortable so we can come out of our shell more.

Also, you could have asked to talk to her on the side. In addition, you seem to prefer trying to the online dating thing. My suggestion is to stop worrying about dating the co-worker. The reason why I say this is that, you do not seem sure about her and every post, you say I will do the online dating. Focus on your profile, this is the new era, meeting someone online (as long as they are not a nut job) is no longer taboo. Hell meeting someone at a bar, is considered taboo at this point lol.

I wouldn't say it didn't go well, just not what I had hoped. Once the crowd dwindled down to about 6 people, it was better. These issues are more than just weight. I have had this issue ever since elementary school. Going up and starting conversations has never been a strength of mine. I didn't make many friends in school and I wasn't overweight then. I wouldn't say I excel at one on one but rather I'm better at it. Where I really excel is by texting or written communication. I'm a completely different person when I text or use instant messenger vs face to face.

I think I already moved on from this woman at work before I went. I choose online dating because my strength is in written communication. I can approach people easier by messaging them than in person.

Well now it is time to start communicating with other women. Online dating is not bad. Just be careful of which sites you use. You never know.

I was on eHarmony over a year ago and liked it. I wasn't ready and still weighed over 400 pounds so I didn't have any pictures or completed my profile. That's where I first found out this woman from work was single. I'm writing drafts of my profile and looking to stage some pics so I'm ready to go right from the beginning. I may expand to Match. The free sites seem to have mixed results in my area. More unsavory people.

i did Match for one "free" week and meet a ton of guys..... My current (Tim) being one of them.