Dating Tips for the Shy and Awkward

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Shy woman looking downwards

Shyness is a social anxiety millions of people experience. It’s not as rare as it may seem, because while there are certain habits shy people usually exhibit, there are plenty of folks out there who can hide their shyness very well — myself included. Being shy is a very common issue people deal with when it comes to socializing. And unlike some guys who can use the “nice guys finish last” or “friend-zone” excuses to explain their dating woes, it’s not often we hear about the experiences of women who aren’t finding success in dating. One of the many reasons is that women are dealing with shyness or feeling awkward while dating.

What’s a shy girl to say or do during a first date? Like me for instance; I used to be extremely shy in grade school, and when I got to middle school it died out a bit, and I became more outspoken. But that didn’t mean I wasn’t shy anymore. I’m still somewhat reserved when it comes to social events, and at times I tend to find myself victim to extremely awkward or embarrassing moments, which further heightens my anxiety. So when it comes to dating or starting a conversation with someone of interest, there are times I find myself at a loss. But the good thing is, as I got older, instead of fighting who I was, I found a way to cope with my personality. I try my best to just do things to the best of my ability and get it over with—it’s a challenge I take often because it strengthens me. I have the same outlook when it comes to dating; it’s either we find something to talk about or we don’t. I will however put in an effort, so I don’t ponder the dreaded, “what if?” question.

Below are some ideas that helped me reduce my feelings of shyness while on a date:

Talk about something you’re Familiar with

Find a way to make yourself comfortable by talking about something you like, or have a high interest in. I prefer to start talking about something funny and interesting. Talk about a not-so-common fact, or something you have firsthand experience in. Nothing corny, explicit, or controversial. The point of doing this is to help lessen your feelings of nervousness, and to start a simple conversation that will engage your date. You can weed out people by doing this. Is he (or she) interested in what you’re saying? Do you require someone to show interest in a subject you enjoy and are passionate about? See the next step if this doesn’t go too well.

Asking about Favorites

What better way to start a conversation with someone you don’t know than asking them what their favorite movies, stores, TV shows, or books are? The best part of doing this, is that it can expand into a long ongoing conversation, or it can be quite short. If the responses are short, that’s what the word why is for. If his (or her) favorite movie is Star Wars, ask why. This question always gets people talking. It may end up being the only thing you talk about, and help segue into other cool stuff to talk about.

Talk about a Book

This is similar to the above, but say you have one book (or two) that you both like. If you’re both readers, be creative and plan a date where you each come with a book you like, and review it with each other. Or choose one book to read, and when you’re both done reading, set up a date and talk about it. This activity may give you the opportunity to hear their personal thoughts, moral standing, and opinions.

Games and Adventures

What’s not to love about games? When I first opened myself to the dating scene, I chose places that would force me to interact with my date and have fun, because I hate quiet dates, which often leads to awkward situations. However, playing games helped me relax and ease my nerves. Bowling alleys, miniature golf, amusement or theme parks, and arcades are good places to go. The only downside is, if you or your date have competitive personalities, it may not be as enjoyable. If you’re not competitive, but your date is, use the time to take note of it. Because maybe you’re not fond of competitive people, and participating in these activities will also help you weed out someone you don’t want. Either way, you’re only there to have fun, talk, and get to the know the person, not win a trophy.

Ask about inspiring, life changing moments

Everyone has an amazing story to tell even if one doesn’t think they have a story to share. We’ve all experienced something in our lives that either changed us, or changed the way we see the world. Be careful though. As mentioned above, you might want to avoid talking about controversial topics or politics (if you don’t share similar beliefs). Sensitive topics can bring weird tension when you just want to have a good time—that can easily kill a good date. But it depends. It’s important to be specific in what you ask. To play safe, just ask about a positive experience because you don’t want your date to mention a horrible experience that will trigger emotion and place you in an awkward position you don’t want to be in. Speak up and be clear.

Find the common ground

The more you talk and are hopefully paying attention to what your date says, you may find something you have in common with the person. Finding something in common with someone you’re trying to know better is the goal—compatibility. If not, there’s always a round two date….or not.

There are plenty of more ways to control shyness while dating, without necessarily morphing yourself into something you’re not. These worked for me — if you know any more, share them.

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