Most Helpful Guy
Take reasonable precautions: talk to him for a while online, only meet him in a public place for an hour or two, and leave if at any point you are afraid for your safety.
You have to decide if you even want a relationship right now or if this is something you feel you should be doing due to societal pressure. Like, if you do actually want someone in your life but were feeling nervous due to inexperience dating, I would encourage you to go for it. However, if you weren't even sure you wanted to do it, I'd suggest you figure tthat out first.
Most Helpful Girl
A couple of things come to mind. If he suggested a date after "a very short conversation online". I would question his motives. The last thing you need is someone who wants a random hookup; that will utterly destroy your already floundering self esteem.
Is this a dating site or some other online media? I'd be more inclined to say go for it if it were a dating site.
If you want to meet him, plan initially for a mid-day meet up at a Starbuck's or something. Safer to meet in a crowded place and mid day means you can plan an escape if you need one by claiming plans later.
In dating, you are going to meet many different guys. Some will be good for you, others will not. I stick to my guns about one thing; if you already have a lower self esteem do NOT have sex with anyone early on. Nothing wrecks even a confident woman's mind more than when a guy sleeps with her and moves on.
Yes, you should take a chance. Don't have really high expectations, though, just set your mind in having fun at the moment. You will have to get out there eventually, why not now? Keep your guard up and be safe.