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As a dating advice expert, singles are constantly asking me how they can possibly make it through yet another Valentine’s Day…alone. Let’s face it. This dreaded holiday is only fun for those people who are in love; those who have that special someone in their lives to buy them Godiva Chocolates, a dozen of red roses, and lots of sparkly diamonds. It’s especially great for them.
But what about for the rest of us? For those of us who are single, Valentine’s Day is the one day of the year that especially sucks. What are all of the single people to do on this holiday while all the others are gloating in the glory of this completely annoying holiday? Dean is here to assure you that Valentine’s Day doesn’t have to suck this year. There are things that you can do to not only survive this tactless holiday but to almost enjoy it as well.
If you are single, the most important thing you can do is to convince others that you are desirable. This simple act will not only make others think twice about their feelings toward you, but it also might actually make you start feeling good about yourself too. Remember, in the dating games, men typically like women who they can’t have. This is why it’s especially important for us singles to show others that we not easily obtainable.
One way to do this is to send yourself love letters, flowers, and candy this Valentine’s Day. It’s always important to do this in a public setting where lots of people can marvel at the gifts you have received (from yourself). If you work in an office environment, be sure to draw lots of attention to yourself at a time when you are most on display. For instance, during an important company meeting or at a business event that many people are required to attend. Or, if you’re in school, be sure to have your gifts arrive during an important test when the room is especially quiet. Trust Dean. When that somebody you’re interested in sees that you are receiving attention from someone other than him, it will suddenly make him think twice about his feelings toward you. (Note: As we once learned from the movie, “Clueless“, it’s also a great idea to wear an outfit that shows a little skin because this reminds boys of being naked, and then they think of sex.) You’ll soon see, after all of this faking, at the end of the day, you’ll not only have won the attention of others, but you’ll also have lots and lots of great gifts (like chocolate) that you won’t be forced to share with anyone (because in reality you’re still single).
If spending money on yourself or writing love letters to yourself seems like too much work, there are other things that you can do this Valentine’s Day so that you technically don’t have to be alone. One option is to create a contest to find yourself a boyfriend. Post an ad on Craigslist, write a blurb on an online dating site, Tweet, post on your Facebook wall, or better yet host a contest on your blog. (Check out the Date Dean Contest to learn more ideas on how to launch a successful contest to acquire a boyfriend.) The great thing about this option is that at the end of the contest, you actually have a real live person to date on Valentine’s Day.
And lastly, if none of the above options seem viable for you, you can always ask one of your hot single gay friends to act as your boyfriend this Valentine’s Day. If he’s a good gay friend, he’ll want to do everything in his power to make you to feel like you actually have a boyfriend this year. One way to make this work for you is to show him lots and lots of pictures of all of your ex-boyfriends on Facebook and in your phone so that he’ll know who he has to put on an especially good act for. It’s always great to have your gay friend give you a soft smooch you on your cheek, hold your hand, or gently stroke your hair during that “unexpected” encounter with your ex. Trust Dean. Your ex will not only be feeling jealous of your hot new “boyfriend”, but you’ll also be feeling pretty special too. It’s truly a win-win for everyone involved…well except for your ex. (Note: if your gay friend tends to have a high pitched voice or often wears lots of bright pink accessories, you might want to ask him to tone it down a bit just for the day. Remember, the point of having a gay boyfriend in the first place is to have him help you convince others that he is your straight boyfriend.)
We all know that Valentine’s Day is the worst day of the year for singles. But with Dean’s simple dating advice, this year can be the first year that you actually survive this dreaded holiday unscathed. Whether it be writing love letters (to yourself) or adopting a gay for the day to act as though he’s your boyfriend, you don’t have to participate in the lonely hearts club any longer!
If you have love in your life, then cool. Love the one that you’re with. But if you don’t have love in your life this Valentine’s Day, remember to simply pretend to others like you do. It’s a harmless little white lie that will surely make your heart glow lots of red this Valentine’s Day.

On V-Day, I like to say a lot of “awww’s” from my cube at work and tell everyone how I just got another sweet text from Jake (my fake boyfriend). I even once went so far as to create a fake Facebook account for “Jake” and would post as Jake on my wall how beautiful I was and how I couldn’t wait to see me soon.
Dear Cindy!
Thanks for your comment! Those are some great examples of how to fake it to make it on Valentine’s Day. I can tell from your brilliant ideas that you must be dating professional as well. I have never gone as far as to create a Facebook page for an imaginary boyfriend before. But this sounds like a a great way to prove to the World that you are desirable! Great work!
Happy Valentine’s Day to you (and Jake).
Love,
Dean
I have played many the part as “straight” boyfriend, but where is the compensation?! I will never leave my female friends hanging – I am a shoo-in for the role as “Man Friend” – so I have been known to don some straight apparel, skull a quick brew and scam on some tail…all in the name of friendship, but what about when I’m lonely or in need of an escort. This situation cannot be flipped.
Dean, do you have any suggestions for the straight girls out there to reciprocate the “love” for their gay best friend counterparts?
Dear Browniepants,
First, I would just like to give you a sincere mazel for continuously playing the role of a straight boyfriend to all the lonely single girls out there. Your willingness to help others in their true time of need and your courage walk the streets as a straight male has certainly not gone unnoticed. You are amazing.
Now moving on to your question: You are right. There is no way that a straight girl could ever pretend that she is your boyfriend for the benefit of making other men believe that you are a couple. It just doesn’t work in this type of situation. But, with this being said, straight girls are not a total lost cause. They might not be able to play the part of your fake boyfriend, but they can certainly be a wingman for you. They can talk you up at a bar or better yet they can always introduce you to some of their other gay friends. And if neither of those options seem viable, keep in mind that a straight girl makes a great companion for shopping. A trip to the mall together might not help you to score a boyfriend…but if a straight girl can help you to make wise decisions about your wardrobe, I’m sure you’ll have no problem at all scoring yourself a man while sporting your new duds.
Oh, and Browniepants might not be the best name to use when you’re trying to attract men. Because Browniepants kind of sounds similar to brown pants….and we all know what that means!
Here’s to lots and lots of love in your future! Because you deserve it!
Love,
Dean