Dating in your Thirties: Valentine’s Day Edition

It’s Valentine’s Day—a day that most men wish would permanently go away and also a day in which women tap their feet waiting to side eye their significant others when they’ve sent no flowers or chocolate, or made no dinner reservations. As illustrated below, Valentine’s Day can be equally frustrating for those of us dating in our thirties: 

What Do You Get Your Friend With Benefits?

I pick her up after her bartending job.  She smiles as she hops into my car and starts to make small talk.  I return a half-hearted smile and hope she doesn’t talk me to death—it’s late and I’ve had a long day at work.  We get to my place and I grab something to eat while she showers. I shower after catching up on the news and we both head to bed.  She leaves before morning.  This is our routine about two to three times a week.  We rarely speak other than when she comes over for what she calls “love making”.  She recently mentioned wanting me to hang out with her friends.  We all know what type of relationship this is—friends with benefits and nothing else (for me at least).  Now today is Valentine’s Day and I’m wondering whether I should get her something.  She is not my girlfriend nor will she ever be.  But she’s probably expecting something since we’re sleeping together, right? If I take her out will I be sending her the wrong message?  I don’t want her to feel bad, but I don’t want to mislead her either.  I don’t want to end this friends with benefits thing we have going and I’m worried that if I don’t acknowledge her on Valentine’s Day, then this might be it.

I Took You Out For Valentine’s Day–Now What?

coffee shopWe met in a coffee shop. Our encounter was brief but sweet.  We talked about the book I was reading and he recommended a book for me to purchase.  After a few phone calls he asked to meet me for a drink.  I was hesitant at first but decided to go anyway.  We shared a few laughs but I knew immediately that we could never be more than friends (I’m picky intuitive).  After a few flattering remarks about my beauty and enjoying our conversation, he asks when we can meet again?  I begin to stall, hoping he can’t see the anguish on my face.  “How about next Friday,” he proposes before I can think of a response.  I check my calendar to stall for some more time, and realize that Friday is Valentine’s Day.  “That’s Valentine’s Day,” I declare while trying to think of a quick response.  “So, it can be our first official date.  Wouldn’t that be romantic?” he replies.  I give him a blank stare until he uncomfortably changes the subject.  Am I wrong for not wanting to go out on Valentine’s Day with a man I don’t like nor want to be romantically involved with?  I don’t need a romantic dinner that badly.

She Trying to Pick Up A Valentine in the Club

The music is glaring and I spot her across the room.  She is making her body move like a contortionist and I can’t help but two step my way over to her so that we can rock to this “Drunk in Love” remix.  We dance to three more songs and I’m lost in her rhythm.  It’s almost like we’re the only ones in this club.  I ask to buy her a drink and with sweat causing her face to glisten slightly, she smiles and walks with me to the bar.  We try to have a conversation over the blaring music in the background.  I want to see her again, if only to move my body to the rhythm of hers one more time.  Before she walks back over to the sea of men on the dance floor, I ask to take her out.  “I would love to!  How about this Friday?”  As the words rolled out of her mouth, it was like the DJ brought the music to a frightening halt.  Did she say Friday? Valentine’s Day?  This chick wants me to take her out on Valentine’s Day.  As the dollar signs start rolling through my head like a slot machine, I tell her I’ll give her a call later in the week to confirm.  With my drink in hand, I walk over to where I was standing hoping to find another beauty who isn’t interested in a Valentine’s Day date.  Should you expect to be taken out for Valentine’s Day on a first date?

I sympathize with the pressures that this one day seems to carry for both men and women.  Valentine’s Day has always been a special day for me because it is my Ace’s birthday.  I am not fussy about presents, so I have never placed a lot of pressure on my significant other to go above and beyond on that day–I’ve always preferred that he demonstrate his love in simple ways throughout the year.  Whether you are bemoaning the day, or posting posting your gifts on Facebook and Instagram, take the time to remind those you care about how much you love them.

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One Response to “Dating in your Thirties: Valentine’s Day Edition”

  1. undercontract Says:

    Maybe it’s just me, but single or not, Valentine’s Day does nothing for me. I believe that relationships should be filled with romantic gestures all time and just because. Honestly, who waits for one day out of the year to give someone flowers, take them to dinner or “show” them that they love them? The holiday is utterly ridiculous. I expect for the man in my life to do special things for me frequently and randomly. I’ve never cared much for the holiday. I think any woman in her thirties who is determining her worth or her significant other’s feelings for her based on his performance (or lack thereof) on February 14th has some serious evaluating to do…

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