Dating SOS: I need your help, dating is leaving me clueless…

Double texting. No messaging after 7PM. Avoid serious topics…the list goes on and on. Who knew there were so many rules to ‘dating’? And to be honest, I’m having a hard time navigating them all. 

Life was much simpler back in the day, when my only thoughts on love were that of fairy tales and Prince Charmings — he always seemed to just magically show up, and they’d live happily ever after. Now, at 29, I know better…finding love doesn’t work this way.

It requires work. It requires time. It requires a whole lot of patience. And yes, it may even require failure.

In the past, this is something that I’ve found intimidating. Worried of looking dumb or sounding stupid. On a first date, what do you do? What do you say?

So, I never really put myself out there to try…until now. | Dating SOS: I need your help, dating is leaving me clueless...

I was talking to my brother about a potential suitor, whether or not he was interested, am I mixing signals, etc. I know, my brother is the greatest. He asked me this question that left me completely clueless: Is he double texting you?

Please tell me I’m not the only one who had no clue what this means. Here’s what Urban Dictionary had to say:

Sending two texts in a row without a reply in between.

Easy enough, right? According to my brother, this is a sign of interest. I don’t know whether or not this is true…but I’m learning that in the world of dating, there are many rules and social cues I’m supposed to follow.

Ultimately, I’m just going to continue to be myself, and whatever happens, happens. But if there are things that I should keep in mind, I am definitely open to hearing them. 

I could Google all day long (spent some time doing that today). While Google is great, I want to hear for you! From your experience, what are somethings I should keep in mind for my own dating journey?

What are some great conversation starters I should try?

What can I do to continue to spark interest? 

Let me know in the comments below — I’m really looking forward to what you guys have to say. 2019, I made a new years resolution to get out of my shell and try new things. We’ll see what happens next leading into 2020…

Until next time,

xo Maya





Maya is owner of Pink Caboodle, specializing in Fashion and Body Positivity.

  1. Fear Pink Caboodle,

    Your plight is an interesting one. Like you, I have no clue of the right answer to your dating Selena. Perhaps, there is no “right” answer.. Of course I am a man, and of an older generation than you, I often say that if I had to begin dating again, I would be lost. When I began dating my wife, I simply told her that I liked her. While she hardly took me seriously, at first,, at least she knew my thoughts about her. It was awkward, at first. I was awkward. I was not quite the Casanova that I would later become. And, she had to see the best in me despite all my faults…and vice versa (of course, she would say that she has no faults). But, at the end of the day, we had to be our real selves. Talk to each other…get to know one another. Allow ourselves to be flawed. And, determine if we can love each other past the flaws. It’s been 37 years, since I told my “boo” that I liked her…and I still do.

    So, I do not know today’s rules. The only thing that I know is that the rules of dating are different today than they were 40 years ago. But, I can say that you need to be yourself. Know who you are and whose you are. Know that you are awesome. Walk in your awesomeness. But also be vulnerable enough to take risks. Let him know that you would like to get to know him. Ask him on a date. And remember, he may not be a Casanova. He may be just as awkward, nervous, and confused as you.feel you are. You have nothing to lose and it may take some of the pressure off him.

    Best wishes.

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