My dad sent me this…he sure does know his little girl well 🙂

I’ve never had a successful Valentine’s Day. The closest I’ve come was when my college boyfriend sent me on a scavenger hunt…but here’s the catch: he didn’t know he was supposed to have a surprise at the end. You know, to make all of that running around campus worth it. Minor detail. Anyways, other than getting some good cardio that year, I’ve never had a great experience on Valentine’s Day. Not because I have had bad experiences, but because I haven’t had any traditional experiences. I’m serially single on February 14th. I’ve dated men here and there during the red and pink season, but none of those flings were ever in a place where I’d want to celebrate a holiday about love. I’ll take Chinese food with my gay best friend instead, thankyouverymuch.

As I sit here on Megabus, trying to outrun the snow storm to NYC, I’ve begun to reflect on the situations that compel me to spend five hours on a bus to be with my male friend who isn’t even attracted to women on Valentine’s Day. What are the worst kinds of relationships to be in when February rolls around? Some of my list is based on personal experience and some is from my imagination, but I guarantee all singles this simple fact: you don’t want to be in one of these not-quite-relationships on February 14th.

1. The OK Cupid Relationship

Online dating sites are responsible for tons of successful relationships. Most of my friends have met their significant others on OK Cupid or Match or Tinder (but seriously, if you met on Tinder, don’t tell anyone). All of the success is good and well, but odds are you’ll simply force yourself to go on multiple dates with someone just because they are normal compared to the sea of weirdos who flood your inbox. Example: Last time I used OK Cupid, the following was one of the messages in my inbox: “Hello! I’d like to get to know you. This morning I lapped milk from a bowl like a kitten, but that was the most interesting thing I did today. What about you?” Taking that winning intro into consideration, along with screen names like “blackmeat84” and “want4u2luvme,” pretty much anyone on a dating website with a job, basic hygiene, and common manners seems worthy of a second date. DON’T DO IT. Especially not on Valentine’s Day. You’ll trick yourself into liking someone just because they’re OK with Cupid (get it?). That, or you’ll have a stage 5 clinger on your hands come February 15th. Trust me, newfound online interests are pretty much the worst things in which to involve yourself on Valentine’s Day. Do yourself a favor and avoid the awkwardness by pretending you didn’t see their text.

2. The Ex Relationship

Ending a relationship shortly before Valentine’s Day makes February 14th switch from being a hokey Hallmark holiday to a distressing evening that you spend imagining your former loved one cuddled up to a desperate wannabe-you. Or just a nice girl whom you can’t help but hate. But she’s probably awful. Anyways, I think the only month during which you should be allowed to break up with someone is May. That way, you have the whole summer to get over the person- plus you’re naturally happier when you aren’t a winter hermit. By the time February arrives, ex who? Really, at all costs, avoid breaking up with someone November 1st -February 13th. It’s just not worth it.

3. The Frielashionship

A friend-relationship mash up is the definition of complicated in February. Odds are, one person likes the other way more seriously than the other likes them. Two years ago, I learned the hard way that I can’t just ignore the signs that a male friend likes me and expect him to act like a normal person on Valentine’s Day. I got a red heart-shaped vase with two dozen roses delivered to my apartment. First of all, kudos to the delivery guy who climbed the six flights of stairs leading to my old walk up in Manhattan. Secondly, what was I supposed to say to my friend? “Thanks for the flowers but I’d rather be single than date you- isn’t it obvious?” I mean, there’s really no good response. I said “thanks for the flowers” and then never saw him again. We clearly weren’t the best of friends, but still- Valentine’s Day will surely ruin any sign of friendship with someone who wants to be more, so go ahead and clear all of that up before February 14th. Rip off the Band-Aid.

4. The Imaginary Relationship

No better day than Valentine’s Day to remind you that this relationship is 100% in your head. Snap out of it! I don’t care if this is an office crush, a celebrity obsession, or your second cousin. You don’t have a chance of ever feeling their perfect arms that you’ve creepily studied wrap around you. They are not subtly flirting, they aren’t playing hard to get, and they don’t wish you’d make a move. Get your mind in check before Valentine’s Day so that you don’t suffer a pseudo broken heart. Particularly if this person already has a special somebody…no relationship is worse than the one where you can’t accept the truth. Pull yourself together!

5. The Undefined Relationship

An undefined relationship is generally not a lasting relationship. Take it from me. If you’ve been “together” for months and he still refuses to call you his girlfriend, then you’re in for some emotional trauma. Ben & Jerry better be waiting in your freezer, because they are the only men who will make plans with you on Valentine’s Day. If someone has a fear of commitment, Valentine’s Day is sure to ensue panic. They’d rather jump in a pool of snakes than take part in this loaded date night, so you might want to call a spade a spade before their disappearance surprises you (which it shouldn’t).

Godspeed, and Happy Valentine’s Day!