Starting to date


I'm a 27 year old guy, turning 28 soon. It may sound a little strange but I've never dated, had a girlfriend, or really asked a girl out.

I was wondering how to start the process of actually meeting women and asking them out. I recently joinied an online dating service. My biggest issue is probably that I'm extremely shy. I have a decent job (consultant), decent education (three bachelors, and and MA and in decent shape (normal weight and height, at the gym 5-7 days a week).

I was also wondering what women would think of a 28 year old guy who's never dated before, who's never actually kissed a girl or has asked a girl out before? Would that raise any red flags?


Most Helpful Girl

  • So is the reason that you have never dated because you never wanted to be bothered with it all, or just for the fact that you are so shy? I find it hard to believe that someone so accomplished is so shy...but I guess it happens. the older I get I get more picky I get.i don't look for the same things that I used to so don't be too hard on yourself about it...Mature women would actually rather find someone such as yourself believe it or not..You have a lot going for you and don't worry there are no red flags..just don't make it an issue with them. But If you end up asking someone out and they turn you down, then you just keep trying. but again I find the biggest problem to be lack the of options if ya know what I mean..It is way more difficult the older we get to meet people worth spending time on. I am sure that being educated you have certain standards, right?! well this makes it more difficult! Yes you are different! but certainly not in a bad way. So when you do finally ask people out they don't need to know all of that stuff until you are comfortable with telling them this...just be yourself and tell them all of the great things you have going on and be confident about who you are and what you do. women love that! and most of all be yourself!


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What Girls Said 1

  • I don't care... if he's been with a girl or not. I think if the girl you meet is mature enough, she'll know life develops differently for everybody. It doesn't matter to me if he's never kissed a girl before. You don't necessarily have to tell anyone, if you don't feel like it, but there's nothing wrong with it. That isn't a 'decent' education-- that's a very good one. :)


What Guys Said 1

  • Wow. How have you avoided women this long? From my experience at that age, the best way to meet women is through your friends. I have a big group of friends that all hang out together, and when ever we go out, someone usually invites some of their work friends. So my advice, talk to one of your buddies and have him ask his girlfriend if they have a friend that might be interested in you.

    As far as women thinking that is strange, yeah, they might. But don't worry about that (or talk about it either!). Just remember. Women like it when guys are friendly, playful, respectful, and confident. It is all common sense really. Just remember to smile.

    Good luck buddy.