Getting Over First Date Insecurities

Published on Author GG RayLeave a comment


Eventually, unless you have decided at a young age to become a monk, you will have to go out on a first date with a member of the opposite sex. Having said that, the odds are very good that if you play your cards right, you will go on many first dates.

But no matter how experienced or inexperienced you may be in the dating arena, only a select handful of men (Tom Cruise, Barrack Obama, and possibly Mick Jagger – to name a few) go on dates without worrying about a thing.

For the rest of you, however, it’s hard to quiet down the nagging insecurities that are inherent when going one on one with a new lady. This article will point out a few of the more common worries that men have and some tips on how to overcome them.

Physical Appearance

Okay. There is no magic transformation machine that can change the way you look overnight, so forget any last minute miracles. Just remember this – she never would have said yes to begin with, unless she was attracted to you on some level. Plus, women tend to be less appearance based in their decision in men, so your charming manner may be what got you her number in the first place. Here are a few tips to make the night go smoothly:

1) Dress appropriately. If you are going to a movie, then you don’t need to wear a 3-piece suit. Pick an outfit that matches the evening. The last thing you want to do is to make her feel over or under-dressed, which will only leave you both feeling awkward. A good tip is to let her know this in advance. For example, when you ask her out tell her that the restaurant you are going to is casual/dressy, that way she will know what to expect.

2) Shave. Make sure you shave before you go out. Most guys ‘stubble-up’ by the end of the day, and not every woman likes a scratchy face.

3) Cover-up. If you have a feature you are trying to downplay, say an extra 20 pounds, then don’t wear pants that are tight. Try not to draw attention to any feature that you are uncomfortable with, otherwise you will be insecure about it all night long. Plus, just because you are worried about something – like you potbelly – doesn’t mean it bothers her.


A lot of men blow it the minute they open their mouths. There are several ways to avoid this problem, and none require a lot of effort on your part. One of the most important things you can do to help a conversation is to be a good listener. If you actually show that you are interested in what she has to say, she will be more relaxed. But you also don’t want a veil of silence to descend on your table. So if you are one of those stammering nervous types who ends up talking about sports for two hours, try a few of these tips to help ease the panic:

1) Be topical. Before you head out for the night, read the paper. If you don’t have a paper handy, then hit the web and find out what is happening in the world today. And not just sports, check it all out. Knowing what is happening in your city is excellent, especially if it leads to something she didn’t know about – a new restaurant, a cool café, an up & coming band, etc.

2) Movies & Books. Opinions are welcome, especially when they are on topics that you can speak with confidence on. If you can read a popular novel once or twice a month, then you are ready if you have asked out a woman that likes to read. Movies are always topics of conversation, so be prepared to offer up info on movies you’ve seen. The same goes for TV. Watching reality shows has become a national pastime, so make sure you have an idea about what is one the tube these days.

3) What to avoid. Politics, religion, any prejudices you might have, boring conversations about your job, ex-girlfriends, current girlfriends, stupid things you do with your friends, sex (at least not right away), your ex-wife, and stories about things you did while you were really drunk.


If all goes well at dinner, then you might be able to parlay that smooth talk into some loving. Of course this is when the real insecurities kick in, since up until this point there has been little, if not any, physical contact. Most guys know that a kiss can make or break a relationship, and if you didn’t know that you do now. The reality is that up until now, everything that has happened has been in your control.

First, you got over the hurdle of asking her out on a date, and she said yes. Second, you planned the date, so you were in control. Third, the conversation went better than expected, and there were other people around to keep things less private. Now, however, at the end of the date you are alone and there is the expectation of that first kiss. In order to do it right, follow these tips so you know what to look for:

1) Body language. This is a tricky one, since her body language could be telling you one thing but mean another. For example, she may have been bored with the date, but is still physically attracted to you. This means she has been dying for some physical contact, and expects more than just a kiss. Normally, if she is making eye contact, not yawning, touching you frequently on your arm/shoulder/leg, then that is the green light that she expects a kiss.

2) Hug or Kiss. Always, always, always kiss her! The worst thing that could happen is that she turns away, but failing to kiss her may signal to her that you either dislike her or are not interested. Put the onus on her to rebuke your kiss. Do not end the night with some lame ‘buddy hug’, which will make her think that she is your sister. The tongue is optional if she responds well and comes back for seconds.

3) Eyes. Close them. Open eyes signal boredom or fear. The more passionate you are, the more likely you are in getting an invitation to step inside.

Final Thoughts

You know you should relax, but you need to remember something even more important – make her relaxed. You asked her out on a date, so the expectation is that you are going to be in control. Nobody likes a nervous driver. Be calm, stick to your plan, and she will respond positively. And if things don’t go well, try, try again. Remember, there is nothing bad about dating several Mrs. Wrongs, before you find the one that you like.

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