DATING

Single Men’s Guide to Securing a Valentine’s Date

Marie Osmeña
3 min readFeb 5, 2024
man looking with love on his face
Photo Cottonbro Studio by on Pexels

Feeling a bit jittery about Valentine’s Day rolling around?

Many of you must be, now that the season of love has rolled around again. Some are even busy planning out for dates, while some…are worried because they don’t have anyone to go on a date with.

Don’t worry, I’m here to give you a helping hand.

So, if you’re a single man who is thinking about securing a Valentine’s date, this guide’s for you.

First up, be prepared.

Condition yourself and think about it thoroughly — are you really up for this?

Do you really want a date for Valentine’s Day, or is this just you wanting to get your nosy relatives and coupled-up friends off your back?

If you’re positive that you are, then you need to prepare. The holiday isn’t that far away and you can’t just walk up to some pretty stranger and ask them out.

So if you haven’t been on a date in a while, you’ll need to dust off your book of conversation starters, update your date night wardrobe, and get ready to mingle.

Now, let’s talk about confidence.

Yes, it’s a bit of a cliché, but having confidence really works.

You need the kind of confidence that makes you feel good about yourself and shows that you’re comfortable in your own skin.

Emphasize what you like best about your looks. Guys can be just as good at this as women — wear a shirt with a flattering color and spritz on mood-boosting cologne. Go to places where you feel most comfortable, such as a dance club when you know you’ve got the moves.

Not only will confidence draw women to you, but they’ll draw the kind of women you also want to go out with.

Be a man of action.

Sitting around won’t get you anywhere.

You need to be proactive. Talk to people, join in, socialize, and make yourself known — may it be online or in real life, you need to be where you can meet new people.

Check out any local events that interest you; it’s a great way to meet like-minded people. You can also choose to give speed dating and joining dating sites a try.

Oh, you might be skeptical about online dating, but they can introduce you to people who you might not encounter in your everyday life. This is especially true if you give international dating a try.

Speed dating has two things going for it: it’s quick and it’s relatively painless. With the right attitude and by managing your expectations, you can have a lot of fun, and even expand your social circle.

Don’t wait too long — Valentine’s Day is on its way. Shoot your shot.

Be sincere.

If, at this point, you’ve given up on sincerity, just remember: nobody wants to go out with a liar. You sure wouldn’t.

But even with sincerity, you need to be thoughtful. Don’t mistake honesty with license to be rude, and sincerity as an invitation to overshare.

When you approach a woman, be clear that you’re asking her out. You can also give her a bit of context as to why you chose to ask her. Maybe you can tell her you enjoy talking to her, and you’d like to get to know her better. Maybe you can tell her the upcoming Valentine’s Day has gotten you thinking about putting yourself out there again, hoping to meet someone special.

And remember, don’t fear rejection.

It’s all part of the dating scene and life.

If someone says no, that’s totally okay. It’s not the end of the world. It just means there’s someone else out there who’s a better fit for you.

So, keep going and stay positive.

There you have it. With this simple guide, you’re off to a good start to securing a Valentine’s date.

Best of luck!

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