Dating Multiple People (and Why You Should Be Doing It)

I suggest this because you’re going to be super-nervous as you begin to date. I know I was when I started actively dating and I’d only been out of the dating world for 4 years in my case. This extreme nervousness is going to have the possibility of creating some bad dates and you won’t be representing yourself very well.

Also, even though I had dated before my 4-year drought I had never randomly and actively dated. It had always been through friends or asking out co-workers. Because of that I felt like I was horribly behind everyone else and that there were going to be all these tricks and secrets that I knew nothing about. It caused me to second-guess everything I did and it only hurt my dating life (because honestly nobody really has all this figured out no matter how much they date). I suspect you’re going to be feeling these same emotions.

So dating actively and often can help you overcome these areas. Here’s what I would say:

Bad Way to Approach Dating: Try to find the perfect person and then date them
Good Way to Approach Dating: Date everyone you possibly can and in the process try to find the perfect person

The “bad” way will create so much anxiety (trust me). This is because with the first method you might be going on one date every 4 to 6 weeks. This puts a huge amount of pressure on you to make sure things work. When you take the “good” approach you allow yourself to have fun and date people even though they’re not perfect and the pressure disappears.

That’s my experience but I do believe it would be true for others as well.

I’ve got a serious issue beyond shyness/love shyness: i’m starting dating for the first time at 29…it’s humilating to admit, but being that this post is anonymous I felt comfortable sharing. I have my life reasons why i’m in this situation. I feel online dating is at least, if nothing else, a way to get something started even if nothing comes of it.

Do you have any advice specifically for someone in my position or should I just go along with what’s written in this article?

Honestly, the way I approached this for myself was just using online dating. This made it easy for me to let women know I was interested in date, at least those online. The profile allowed me to express interest, I didn’t have to turn from shy to confident over-night.

Over time, as I started to have success with online dating, meeting people in the “real” world actually became much easier. I started asking women out at parties and had a lot of success doing so. For me, this was mostly because I had so many dates scheduled through online dating that being turned down in the “real” world mattered so much less. A lot of success made the possibility of some failure much easier to accept.

For women, I’m not sure if the same would be true since men do most of the pursuing. I guess you would want to be intentional about showing interest…and success with online dating could make this easier. I’m not the best person to tell women how to flirt but I did find this article which seemed pretty good. I know that if a woman were taking these approaches with me when I was single she definitely would have grabbed my attention.

Obviously many of these approaches are difficult when you’re shy but hopefully some success with online dating could make it easier. Barring success with online dating, you might just start with the easier steps like smiling a lot.

Im a little shy as well, mainly introverted. I dont talk a lot, nor have a a lot of friends. I get a lot of attention, but find it hard to actually be comfortable with people. Ive been told I can come across as sort of mean and self-serving, which is not true really. Im just anti-social and not a people person.

How do I let others know that I mean well and am interested in a relationship?