Tried-and Tested Dating Tips for the Socially Awkward Guy

By Marcus Neo

Are you one of those guys who can’t bring yourself to chat up a girl let alone ask her out on a date? You’re not alone. The good news however is that there are strategies you could use to get your confidence back. And soon, you’ll be approaching a hundred girls a day!

Here goes:

Start in a non-romantic setting

Hold off that first date for a while and start small. Hang out with female colleagues in a non-romantic way. You’ll soon find yourself at ease with women as you slowly gain insights into their world. Pay attention to what they discuss - the latest reality show, movie star gossip, health, or finances.

Alternatively, try spending time with female relatives, aunts, and cousins. The world of women is an intriguing one, and the sooner you immerse yourself in it, the better equipped you’ll be when dating women romantically.

Ask female friends out for coffee or dinner

Now take things a notch further, and get some practice in social settings with women, one-on-one. Call up a female buddy and ask her if she’d like to catch up as you’ll be passing through the area soon.

The goal is to ease yourself gently into spending time with women, one-on-one, in social settings such as a coffee shop or over dinner. Sitting across from a woman, speaking with wait staff, dealing with the check, etc are all useful ways to ease yourself into the social niceties that go along with dating.

Stay true to yourself

Now that you’ve found the courage to ask a woman out, and have landed that elusive date, the best thing you can do is be authentic with her. Don’t pretend to be someone you’re not, or worse still, prep yourself with memorized phrases.

Just enjoy your time with her and let conversation flow just as it would with your female colleagues, friends and cousins. Remember, you’re starting, and baby steps will get you there. In the meanwhile, it’s a good idea to read up on dating advice from experienced experts.

Keep things simple initially

If expensive dinners at upscale restaurants aren’t something you do occasionally even with family and friends, it could be intimidating to suddenly have wait-staff thrust extensive menus and wine lists at you, not to mention the mind-boggling assortment of cutlery laid out.

My suggestion – keep things simple and have a relaxed brunch at a café. Or invite her to a community event, farmer’s market, or a film festival. Choose a location based on her interests and run your suggestion by her.

At this stage, you can still keep things casual by saying something like, “Hey, there’s a Van Gogh installation at the City Museum, would you like to check it out this evening after work?” If she agrees and if things go well, plan well for the next date.

Dating the girl who LOVES to talk

If your girl is a chatterbox, you’re in luck as she’ll be doing most of the speaking. Listen carefully though and ask the right questions to show her you’ve been paying attention. Smile, express shock or amusement, and show her you’re not a bot but someone who feels and genuinely enjoys her energy.

Dating a woman of few words

A time-tested way to converse effortlessly with a woman who listens more is to gauge her interests before the date by chatting with her in advance. Ask her about the books, movies, and music she loved in high school.

If she says she likes JOKER, go a step further and watch a couple of films in the series. If U2 is her favorite band, I’m not suggesting buying all of their albums off the rack. A pro-tip is to look up the band’s Greatest Collection hits (and give them a listen of course). When you meet her in person, you’ll already have something in common to talk about.

The Takeaway

There are no excuses for letting shyness take over your life. Dating can be stressful for women too so why not start off being the guy who is easy to be around instead of the lady-killer who reduces every date to a sexual conquest.

With time and experience you’ll soon learn the ropes, and the women you fancy will be the ones seeking you out.

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