Home Featured 5 Valentine’s Day Struggles Men Should Avoid

5 Valentine’s Day Struggles Men Should Avoid


Another year, another celebration of St. Valentine’s Day. This day is filled with love, lust, and commercials to make us spend $$$, and the hopes and dreams of single and taken women of a romantic night with their HIM. Now there are dudes who know how to execute this day flawlessly, and other dudes who fail miserably. Fellas, you do not want to be the failure on this day. Here are some common pitfalls to avoid as you try to win on Valentine’s Day:

Not making plans ahead of time

Fellas this has happened to me before. There’s no worse feeling than walking up to a restaurant trying to get last minute reservations, only to hear that they are either a) sold out or b) have a 2-3 hour wait. You won’t even look into your ladies grill in fear of the “you ain’t shit” stare. Most people make plans 1-2 weeks in advance; so I would suggest that you do the same. Figure out the exact itinerary, main time and alternative times to go, and where you want to celebrate. It saves you a world of hurt and judgmental looks from more prepared individuals.

For single men: trying to setup a movement last minute.

As many jokes as I see from peoples about side chicks and lonely women on this day, you would think that men would get on their job and set up the perfect storm. You will have single women who don’t want to seem thirsty and who want to hang out with a dude, but won’t go out her way to ask. You have yourself, a man who’s been scouting the scene for eligible women. Two plus two equals four to me! Making the day of “hey I’m not doing anything and neither are you so let’s do it together” call is a 50/50 chance. To increase those odds I would put out feelers of interest with your targeted women and see what they are doing. That way you will be ahead of the game. Worst case scenario? There has to be some kind of V-day singles party going down in your city. Go out and make the dream work!

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Suspect gifts

For those in relationships, you should know your lady well enough that you know her likes and dislikes. If you have a high maintenance chick, then you know you’ll have to make it rain. If your woman is the subtle type, then play to her personality. Either way it should be something cool and from the heart. I wouldn’t hold my breath on receiving a gift either. This holiday isn’t for you fellas!

Breaking up before the 14th

Does this still go down? Have women not figured out this swindle yet? Did I just make it hot for some dudes? Oops. Well if you aren’t in high school and you are reading this, your statute of limitation for this cost saving maneuver is over. If you have issues with your lady, don’t be convenient and split before a major holiday only to reconcile after. It’s in bad taste. Hilarious…but in bad taste.

Finding out how important Valentine’s Day is to women.

Last year I took my stance on this “holiday”. So women I date know where I stand. That doesn’t mean I won’t still go out or buy nice things for her. I understand the concept but won’t be controlled by the concept. If she is into it I can recognize that and participate in festivities. If she tells you she doesn’t really care about Valentine’s Day and it’s whatever, she is LYING!! You better have something thoughtful at least planned, or you will be the guest DJ in the doghouse! It’s cool to show love on that day and do something nice. That mantra of “you should love someone and express it everyday not just the 14th” is great, but when that 14th hits don’t be the Dahlia Llama, be LL or Drake. It will work way better.

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Any other Valentine’s Day struggles to avoid? Any funny stories about V-day struggles? Sharing is caring, after all!



  1. I keep forgetting about Valentines Day. I can't believe that ish is in a few days. It's funny cause I really DON'T care about it, but if I WAS in a relationship, I'd want my man to do something for me because I know he'd do it for the next b****.

  2. lol You're telling them to make plans weeks in advance with only 4 days to go? Y'oun't really want them to prosper; don't lie.

    Going out of your way to pretend that you've forgotten in a bid to surprise her later on could potentially blow up in your face. It works out nicely in the movies, but I'd proceed with caution IRL.

    1. That happened to me once. I spent a really long time talking about the kinda places I wanted to live in and how I'd drive around just looking at architecture and stuff. I was very forward about us living together and him stepping his game up (I was a complete diva about my preferences and being completely demanding about it) and he waited forever. FOR-EV-ER. I was so pissed off. I showed him a bunch of places on our homes.com account and then one day I couldn't log in and then my favorite two houses were the only ones left on our list. I just assumed, 'crap the other places sold!' and I told him like omg you have to get this one before it goes too! and then….SUPRISE!

    2. A long wait later we had a house. I turned all to mush like yes. Yes baby yes and that Armani shirt (that I picked) is LIKE THAT. I died. A slow, sensual beautiful death.

      But I was annoyed.

      1. lol He probably figured it was worth it, and for something that big it could be. I'm not speaking from experience, but I could see it going all kinds of wrong in certain situations.

        1. lol oh aiight thats wassup…..

          you know ya man more than anyone, what type of dude is he? techy? video game junkie? likes to build stuff? or just a reg sit on the couch and watch the game type?

    1. It depends on what kind of guy he is, but most guys don't really expect anything on Valentine's Day.

      Nothing expensive is really necessary. Bake some him cookies, give him a DVD of his favorite TV show, and present it to him wearing a new lingerie outfit. Feel free to substitute the DVD or cookies for something else he enjoys (liquor, video game, etc.) When he sees you in the lingerie, he likely won't even realize you have a gift in your hand, and you get to buy yourself a gift.

      1. U know what ? you are on to something ,he recently started getting into smallville I think we ran through the first season already ; maybe I’ll get the whole season like a box set.

        1. There you go. A Valentine's gift, and on a future night if don't feel like going out, you can grab a bowl of popcorn and watch a few episodes. Don't forget the lingerie!

  3. I once had a dude I had never met but talked to on the phone for a week before V-Day purchase & give me a bouquet of roses. I thought that was sweet until he told me he was waiting for a “proper thank you.” This dude expected me to sleep with him for a bunch of flowers! I didn’t cuss him, but I wanted to, but told him how big of an idiot he was and that I wasn’t screwing him! We didn’t even know each other! I left him standing in the parking lot of the lil restaurant I was at with MY DAUGHTER and I’ve never seen or spoken to that dude again. The roses lasted longer than our whole time talking. People are silly with Valentines Day!

    1. Gil nowadays these girls do it for a $1 ice cream cone, so he thought it was in the back, good for u for standing up and recognizing who you are!

  4. "If she tells you she doesn’t really care about Valentine’s Day and it’s whatever, she is LYING!!"

    I'm cultivating my first legitimate relationship. We've been best friends for four years but we've always done holidays on our own. He missed Christmas. I asked him to spend it with me I have no idea what he did but spending it alone made me trust him more and I sorta threw Valentine's Day out there as an undertone because, I'm excessively rude and diva-ish when it comes to precision and time. You ever call someone hoping they don't answer? And they don't because they're thinking about you yet hoping you won't call? I would care in a 'I'm actually being sensitive and it's making me nervous so I'll get over it but I REALLY care', sorta way.

  5. Not making plans ahead of time:

    The last V-Day where I had a man, I told him I was going to make him a spectacular dinner. We woke up in the morning and he got me some Hugo Boss glasses and a poem (plagiarized from the internet, when I checked). Then he left and was gone all day. I went out and got the finest ingredients. I was going to make him prosciutto-wrapped filet mignon, among other things. Dinner was ready at 7:30pm. He didn't get home until midnight, claiming he ran into friends he hadn't seen in forever and we could have dinner another night. He was a cheater, I later found out. F that ninja.

    My current dude has told me not to worry about V-Day. We're going out one weekend, and on the day, I'm making him a special dinner. I even bought a nice dress. I'm sure he will deliver. He's amazing and the opposite in all ways of that awful dude.

    For single men: trying to setup a movement last minute.

    Going out with a single girl as a single guy on V-Day sends a certain message. It says "I'm interested" or "I like you." If I found out after the fact a dude was only capitalizing on the love in the air (a la "Wedding Crashers") for the cookie, I'd be furious and delete his contact information after the fact. Sure, it'd be after, and he'd already have gotten the cookie, but his karma will suffer, and that'll make me feel better. 🙂

    Suspect gifts

    Eh, I'm not super picky. Mainly just want someone who puts in the thought and effort. It SERIOUSLY doesn't have to be super expensive. It can just be super thoughtful. Like a gift basket with all of my favorite candy, or some silver jewelry that you know would go with something I have. There are lots of inexpensive options that show you care. I'm pretty sure, however, that the better you're doing and the longer you've been together, the more important it is that those thoughtful gifts also come with a price tag. Just to show how you value the situation.

    Breaking up before the 14th

    I've had dudes break up with me before my birthday, or before Christmas. My last FB said he was going to try something real with another FB, see if she could be his girl 'cause he had fallen in love with her, and it was time to do right by here. That was Dec 1st. My birthday is Dec 15th. I didn't realize what he'd done until he texts on Dec 27th talking about he can't stop thinking about me. Meanwhile he's now officially WITH that other girl and has pics of him and her all over Facebook. F that ninja. He's since called and texted me every single week, trying to get back in. Luckily, I met my current (and most awesome) dude on my birthday, and dudes like that aren't even a temptation.

    Finding out how important Valentine’s Day is to women.

    I don't date dudes that don't believe in any holiday, including V-Day. That's petty and ridiculous to me, and just a lie to avoid putting in effort or spending money. I believe in celebrating all the holidays, cooking, wearing the hoilday's colors, all that. No point in me linking up with a dude who's gonna come to the table on Thanksgiving talking about "You know we're celebrating how the pilgrims raped the Native American's culture, right?" Yeah, I know that's what happened, and that's not right, but I'm really just trying to make a feast and spend time with my family.

    1. "My last FB said he was going to try something real with another FB, see if she could be his girl 'cause he had fallen in love with her, and it was time to do right by here."

      *BlankStare – jaw dropped* Dayyyyuuuummmmmmm!!!!

      Katt. girllll l I ain't laughing AT YOU — I'm laughing WITH YOU… *otflmaoooo*

      that ish cray!!!!

      1. Yep. I feel bad for her, though, because he seriously texts or calls EVERY WEEK talking about "I can't stop thinking about you. I couldn't delete your info", etc. I ain't paying that fool no never mind. Unlike HIM, when I get a significant other, I stop trying to talk to other people.

    2. " and a poem (plagiarized from the internet, when I checked)…"

      Done googled the poem? Lol!! That is comedy. I hope you waited at least until after y'all called it quits to check, lol.

      1. LOL. It was obvious. It had words in it like "chickadee". He ain't NEVER used the word chickadee in speech so I was like, "Uh…let me just check." Dude never knew I KNEW.

        Funny (or funnIER) thing is, that was the SECOND guy to do that to me. LOL. Dudes, don't Google "Love Poems" and give that to your girls unless you want to get found out.

  6. I’ve been pretty solid with vdays my only slip up was last year I think I tweeted about what I got my valentine and this other girl was maaaad #begoodorbegoodatit. Other fails include

    Fake jewels: nothing worse that turning ya sweetheart into the she hulk and having her ready to whoop ya ass like well …the she hulk

    Getting led on- as dudes break up before holidays chicks will start talkin to one. I know girls that will give a dude play for a quick dinner n a movie n chuck up the deuces.

    Ball within ya budget- Don’t let YOLO get you gassed.

  7. I really do not give a f^ck about holidays…but I also know I have to do something in order to keep my main happy and appreciated. If it were up to me, I'd just chill and write a blog or something for VDay. However, I will probably be smitten by dinner, lingerie, potential(3some), and lots of gifts.

    I don't like woman to get me gifts on the contrary, but I love to surprise a woman with some fly sh!t that she didn't expect, not necessarily on a holiday though. VDay is like church on a Sunday morning for a kid that just wants to watch cartoons and sleep in. I feel like I am forced to do the sh!t and many women think it's a cop out, but nobody remembers Sweetest Day now do they….

    The ladies on here couldn't even tell me what day Sweetest Day was with out goggling or binging that sh!t could you….IM WAITING LOL
    My recent post Guest Post: Polygamy- PROLLY GIMME A Sister Wife

    1. Sweetest Day is not celebrated everywhere. from my understanding just some places in the Midwest. I'm from the mid-atlantic, and familiar with it though only because I have an ex from out there.

  8. Oooo…one Valentime's Day, I had gone to see an ex in the A, as we were on the 'we gon' try this long distance thing maybe', I got back to DC on VDay, ran into another ex on the train and we got out an, "oh! Hey?" as the doors were closing, went on a blind date with my aunt's co-worker's son – it was very bad and he walked like Kaiser Soze from the Usual Suspects, and just as that day was coming to a close this dude I was talking to asked if I wanted to ride up to Atlantic City with him. I did and came back with like $400. Oohhhh to be young!
    My recent post What Do You Say About Valentine’s Day?

  9. We loved your post about how to avoid another Valentine’s Day disaster! We have all had a few of those in the past. It’s great to be able to share these helpful tips with the Valentine’s-challenged out there! We thought you and your readers would be interested in our effort to make Valentine’s Day a better experience. By following the link below, you’ll be able to view the Top 10 Tips to Avoid A Valentine’s Day Disaster – Advice For Men… From Women. http://youtu.be/gC5bac9HMqs. It's funny, satirical and maybe too real. Enjoy and thanks again for your great post!
    My recent post Click one of the post titles above to include it at the end of your comment

  10. Here me out on this lol

    I’m a single father of a 9 year old girl & 6 year old boy. Last year I was dating the love of my life. Literally, it was amazing. We talked about everything, made the most amazing love, both loyal, no jealousy. Pure bliss. I made this woman feel like she was EVERYTHING 24/7. Problem is, my daughter became jealous, felt like she was losing her father. Would act up & I tried everything. I thought that I was probably pushing myself away from her & giving too much of my love to my girlfriend. SO.. on V-Day, I dedicated my day to my daughter. I took her out & treated her so she knows she is still dad’s princess. Problem is, although my girlfriend got all my attention & love I thought she would understand. Blunder lol She didnt make a deal of it until we recently broke up & its nearing Vday.. Am i the biggest Ahole or was she selfish??

    1. She was selfish. But maybe a better idea would have been to take them both out and explain how important both of your ladies are to you. Or you could have spent the afternoon with your desired and the evening with your girlfriend. A part of her probably understood at the time, but she still wanted to spend that time with you and you can't really blame her for that. Obviously it bothered her since it came out in the end.


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