Also, with men you need to be accessible. Despite not quite being an extrovert, I’ve chatted up strangers in all sorts of places. But I can’t start a conversation with someone who’s always on the mobile phone or always chatting with a group of other girls. I probably could start a conversation with someone who isolates herself with a cigarette far away from everybody, but one or two meh replies will probably make me go away (which is probably more of a problem in a jurisdiction that takes stalking and privacy too seriously and women are quick to dial 112). In short, you don’t need to be in your perfect mood or shape or look or whatever, just avoid unnecessarily blocking yourself off or driving men away. If he starts to talk to you… then he apparently wants to talk to you, so you don’t need to worry about that. Plus, someone in your age group has probably learnt by now that women aren’t born with make-up on and can have a bad hair day. So don’t worry about such things.
Also, defeat the urge to say ‘no’ or deliver the LJBF (‘Let’s Just Be Friends’) as your default reaction when a man pops out of the blue without previous planning or preparation on your part, which is some women’s problem. Instead of blurting out a rejection – or agreeing too hastily and regretting it later – just simply tell him a decision like that is going to take some time, preferably with a cooller head. You can smile while saying that, doesn’t need to sound like ‘Court’s adjourned. All rise!’

If he’s nervous about that, just tell him you don’t want to make a decision either or both of you could regret. Avoid thinking you’re not good enough for a guy showing interest to you or that he’s too good for you or whatever other excuse the scared brain invents to stay passive and avoidant while taking advantage of a fragile self-esteem.

Chances are the man’s nervous like heck as well and it’s costing him some.
Plus, I’d favour walks in public parks over more mood-generating avenues such as dancing clubs, cute dimlit cafeterias, romantic old towns and such like. This is to avoid letting your mind play tricks on you, especially when you’re tired, cold/ill or haven’t slept much or some alcohol is involved. Atmosphere, dim lights, specific music, low hums, voices speaking on a breath, picturesque sunsets etc., tend to work like intoxicating substances. So it can be somewhat like having one drink too many. You probably aren’t going to decide on a relationship at such a fast pace, so don’t allow atmosphere to build up either. Also for the guy’s sake.
Finally, if you can track some insecurities to events in your past, e.g. childhood, for example things like alcoholic relatives or turbulent first relationships or nasty teachers or some of those mild stress/anxiety disorders not few people have, deal with them now better than later. Solving them may also change your taste in men significantly (meaning you won’t like the same guys as much).