You know the saying “you’ll regret the things you didn’t do more than the things you did”?

I think that applies to dating (or romantic relationships in general) more than anything else.

Recently, The Roommate and I have had more than one discussion about wanting to date a particular someone “just because we have to know.”

We have to know what it would be like, what it would feel like, and where it will go.

Sometimes it can be solved with a simple kiss, a single date, and sometimes the only thing that will answer it is full-fledged dating.

My go-to example is that there a guy who I knew in high school and remained close friends all through college, who I still regret not kissing– just to see what it would be like. He is/was quite the ladies man, so I assume(d) he’d make it worth my while… but I chickened out when the opportunity arose. So he’ll forever be “the hot guy I was just friends with.” (Although the rise in my social standing being friends with him is undeniable…)

When those desires rear their heads, it’s hard to think of little else. “What if” constantly plays through my head and daydreams of a first date get themselves carried away and all of a sudden I find myself daydreaming of my wedding with said groom-to-be.

More importantly, there is no real desire for anyone else. As much as I hate to admit it, I’m waiting on Funny Man to get his shit together by the end of the month so we can take our “what if/take-two” to it’s appropriate level and actually date each other. To quote Gigi in He’s Just Not That Into You (I told you, this movie is my life…), “It’s hard to focus on nutmeg when the guy who might be the guy of my dreams refuses to call me.”

I’m a strong believer in fate (possibly to my detriment), so that quote resonates with me on an incredibly deep level. I can easily write someone off as “not meant to be” but when I have this relentless desire to know “what if,” it’s a lot harder to move on.

My impatient instinct is to try to write him off, citing the fact that he has been a neglectful friend. But that’s unfair because the reason I’m having to wait is because he knew he’d be neglectful until the end of March and asked me to wait. humph

I guess this is just me venting about the fact that I hate waiting and I wish it was the end of March so we could get the “what if” answered once and for all.

I’m no stranger to crushes– my diary from elementary school is about nothing except which boy I like that day/week. Sometimes there were multiple boys who had caught my eye. I’m so not exaggerating.

My long-time best friend will not hesitate to tell anyone about my notorious stalking of PK (Pastor’s Kid– rightly named since that is, in fact, what he was) in high school. I’m serious, I literally stalked him in the hallways of my school. What can I say, I loved him! (He holds the record for longest crush with nothing happening– 5 YEARS!)

Since I’ve been single, it’s been rare that I develop a crush. What has tended to happen is that a guy asks me out on a date, we possibly date for a while, and then it’s over. I haven’t had to sit on the sidelines for very long (if at all) because something happens romantically between us fairly quickly. So the sitting and getting butterflies in my stomach at the mere thought of someone or the random Facebook comment that causes me to be “all a flutter” hasn’t really  happened to me.

I had a small crush on A (remember him?), but as I just said, I didn’t have to wait long for things to develop between us when I realized I liked him more than a friend.


A is not who I want to talk about.

I’m telling you all this because I have developed the BIGGEST crush on a guy who I will call Funny Man. I cannot tell you how often he makes me laugh and how easily it happens. Spending time with him has made me realize just how infrequently I find my dates/boyfriends amusing. Yes, we can joke around, but to have someone cause my stomach to hurt from so much laughing is extremely rare. And that’s what Funny Man does.

I’ve been friends with FM for about a year. I play in a energy sports league– we do bowling in the winter, kickball in the summer and flag-football in the fall. It’s composed of only oil and gas people and their significant others. Anyway, FM was on my bowling team last year and I had a small crush on him the minute I met him. He was just getting out of a serious relationship, so I steered clear of him. I was also dating the most boring guy at the time, so FM apparently didn’t make a move either. (FM has given me endless shit about having dated that guy… and it’s rightly deserved.)

My relationship with FM has been purely platonic since we met, and I was fine with it…  until about a month and a half ago. I went to his birthday celebration and I realized I wished to be more than just friends as we shared a chair at the bar we were at. The entire sides of our bodies were touching and I suddenly couldn’t breathe… my heart started racing and I got all nervous.

What was happening? FM is my friend! I don’t feel that way about my friend… do I?

Since then, I haven’t been able to get him out of my head. I have even hung out with him for hours (yeah, including sitting on his couch until 11:00 at night…) and nothing happened. But there seems to be something there. I think…

As I was lamenting about my feelings to The Roommate, I had a revelation.

You know what I said about having had crushes on guys for practically my entire life? I’ve also been the object of crushes more times than I can count. I’ve been friends with a lot of guys and have also dated a lot. Needless to say, I know guys pretty well and I can read them like an expert. It doesn’t help that guys tend to be REALLY easy to read.

But that’s what is tripping me up with Funny Man. I am not able to read him accurately and it’s driving me insane. It’s usually pretty obvious if a guy likes me and I can react whichever way I feel (I can plead ignorance if I don’t like him back or reciprocate the feelings and we end up dating). But with FM, he acts and talks like he likes me, but he doesn’t actually do anything about it. I should mention that he is one of those people who is a natural flirt. He flirts with everyone and is extremely friendly, so then I doubt myself and wonder if I am reading him all wrong.

So he’s left me confused. During a texting conversation the other day, he mentioned wanting to spend more time with me… but no date was set, no plans were made.

There’s a song by the band Say Anything called “Crush’d.” For the last couple months, that song has been on a constant loop in my head when I think about Funny Man. Well, more the chorus:

I have a total crush on you, baby
And I can’t let it go, oh no.
I have a total crush on you, baby
Baby, if only I could let you know.

It’s pathetic. I know. I like him and he sort of says he likes me too, but nothing is happening. I need to just let it go and if he wants something to happen, it’ll happen. If not, well, we can continue the way we are– just friends.

The Roommate said she’s cheering for him– he’s actually likeable and people want to be around him (who knew there were people like that!). If only he would pick up the phone and ask me on a date, I’d be his in a heartbeat.

But I need to take the (very accurate) advice from He’s Just Not That Into You and give him the space to ask me out. It’s actually quite sad how much my life is like the main girl in that movie… but that’s a post for another day.

I’ve been dying to get this all off my chest, so now it’s out there. I’m not afraid of jinxing it (although my track record is not very good in that department), I just want to send those hopeful vibes out into the universe. I need to take the logical stance and tell myself “if it’s supposed to happen, it’ll happen. If not, nothing is lost.” But my logical side is fighting an uphill battle.

This is one of my favorite songs, not just because it’s a catchy tune, but because it’s a really good reminder that life is not a romantic comedy and it’s not going to turn out like we think or plan.

But I can’t help but wish and dream that my next (and hopefully final) relationship will start off with some cute, romantic-comedy meet-cute where we eventually ride off into the sunset, living happily ever after. I can’t seem to shake the fantasy out of my head.

Where’s the line between hope, having a standard, and just being ridiculous? My very logical side of my brain knows that things like a movie don’t happen in real life. But my hopelessly romantic side of my brain seems to spin a very convincing tale to convince my logic, and before I know it, I’m daydreaming a full-fledged fantasy that looks eerily similar to Return to Me, minus the whole heart-transplant thing.

I can’t seem to help myself. And then my expectations are completely out of whack because I start to insist men respond and act like the men in the movies. It’s completely unfair to the men I date, and it’s a complete downer for me when the men don’t match up. It’s ridiculous that I do that!

I know I need to just let the men be themselves and find one that meshes with me in a way no other man has, but I just can’t seem to shake that fantasy man from the back of my mind.

It’s frustrating and unfair to everyone involved, and I can’t figure out how to just let it go. The men I date are flawed humans, just like me. I cannot put the expectations on them that I wouldn’t want put on me. I wouldn’t want the pressure to live up to some skewed fantasy of a guy that in no way aligns with reality.

If I want a man to love me for me, I need to love him for him. Plus, as the best friend, Paul, in (500) Days of Summer says, “Robin is better than the girl of my dreams. She’s real.” I can create the most incredible, dark-skinned, dark-haired man I can imagine in my mind… but he’s not real. It is a complete waste of time and energy thinking about it. There are great men out there who, if I give them half a second’s chance, can show me that they are better than my fantasy man because they are real, their kisses are real, and the connection we have is real.

Now if only my logical side would just tell my hopeless romantic side to shut the hell up!