So a dear friend (who shall remain nameless since I doubt she’d be keen on me sharing all of her business on my blog) just got dumped. She was single for a long time before this boyfriend and in traditional “just got dumped” fashion, fears she will never find anyone else. Now this is total bunk! She’s awesome, she’s sweet, she’s smart, she’s super cute, and she’s young enough that giving up hope now is very premature. So I started thinking about it, and I realized that a lot of my single friends may be waiting for some great guy they find interesting to ask them out. Why? It’s 2009! If there’s a hottie at the Food Co-op, go talk to him. If he’s single and interesting, ask him to go out for coffee or smoothies or whatever it is the kids are doing these days.
Now, you may be saying, but Claire, you are a happily married woman who hasn’t been single in a decade. To that I say, it was a lot of hard work and dedication on my part that got me where I am today. While the first few guys I dated way back in the early 90s asked me out, I spent a good 4+ years in singledom (all through the last half of high school and until the end of my first semester of college). I did have one date (and sorry, if you’re reading this, it wasn’t a good match), but I took a friend to prom (not through lack of trying). I’ve also been the ender of every relationship that didn’t work out. Once I realized I could go find a better match because this one wasn’t a forever keeper for me, it became a lot easier to end a doomed relationship rather than languish in misery for fear that I’d never find anyone else. So, what’s my secret? Be assertive. Here’s the breakdown of the last 4 guys I dated + my prom date who I wanted to date but who didn’t want to date me (sigh).
1. Prom date. We met at Governor’s School the summer before my senior year of high school. I was smitten. We hung out and had a great time. At the end of the month, I wrote in his month book (think yearbook only smaller) that I had a huge crush on him and just thought he should know but please don’t be weirded out because I’d like to at least be friends. Now, this didn’t lead to anything (beyond an awesome date to the prom that friends still talk about to this day). Hell, everyone who signed his month book after me got to read it. But I didn’t care because I was honest and it felt good to get it off my chest.
2. Long distance boyfriend freshman year of college. We met at nerd camp years and years before and had rekindled our friendship during a visit to my grandmother’s house (he lived nearby). There had never been more than a friend connection between us, but he was a great conversationalist, and I fell for the intellectual connection. The catch was I was in Missouri and he was in Texas, so my phone bill that semester was AWFUL! Oh yeah, this was pre-cell phones. Anyway, I decided that I wanted more than just a good conversationalist, I wanted a boyfriend, so I told him. He was down with it and thus began my first long distance relationship. It worked out for a while, but I quickly realized that having a friend in Dallas who is great to talk to is great. Having a boyfriend in Dallas sucks. We broke up after only a few months, but we’re still friends.
3. Oops boyfriend I didn’t mean to date. Shortly after long distance boyfriend and I broke up, I somehow ended up with a really clingy boyfriend in an odd turn of events. See, I wanted to date his friend more than him (and did date his friend, but that’s later), but somehow I ended up dating him. This was NOT me being assertive. This was me going too much with the flow and having to break up with a guy who cried at the drop of a hat (which really makes you feel bad when you’re dumping him). It was a very awkward month of trying to disentangle myself without hurting his feelings. Eventually I had to hurt his feelings or marry him (or kill him which sounded better than option 2).
4. Oops boyfriend’s friend. This was the guy I wanted to date. Of course, by accidentally dating his friend, I feared I had forever screwed that up. But we were friends, so hanging out was a regular occurrence. Shortly after breaking up with Oops, I realized I had only a few weeks before the semester ended and the next year Oops & #4 were planning to room together which would make my life really awkward if I didn’t go ahead and set the stage now. So at about 3 a.m. one night (ah college life) we were standing in the dorm hall talking when I just laid one on him (a kiss, that is). He was shocked! It was pretty awesome & I highly recommend you all do this at least once in your life. I’ve never seen anyone at such a complete loss for words. Even though it didn’t work out in the end, it was worth it if only for that moment. Oh, and I totally ruined the living situation. Oops was NOT cool with the turn of events and things got a little messy. Yeah, I was that girl. Oh well.
5. The keeper. Nate was my last boyfriend before the big break (i.e. 4+ years of solitude) and was always “the one that got away.” When he randomly showed back up in my life (ok, I did send him an invitation to my senior thesis show, but there really were no ulterior motives. We had been really good friends before we dated, and I had spent the following years trying to be friends again. Anyone who has lived this knows what hard work that is.) I was pleasantly surprised and happy to have my friend back. Seriously, no motive beyond friendship. BUT we started talking and hanging out more, and next thing you know, I thought maybe breaking up with him when I was 16 was as big a mistake as I had initially thought it was (which I had thought was a HUGE mistake but one I was too proud to take back at the time. Ah teen stubbornness). Of course, now I think breaking up was a good idea because it allowed us to become who we are now, and I think we would have broken up anyway as teenagers because we did go through a period of complete incompatibility. Anyway, taking a cue from my success years before with #4, I totally took the initiative and wooed him with all my feminine wiles (which included driving all the way to Savannah, GA down I-16, the world’s most boring highway). And here we are.
As a note, with #1, I had no clue if he liked me beyond friendship or not and as we know, he didn’t, so that was a pretty big risk in terms of ruining the friendship. Luckily it didn’t. #2 I though found me interesting enough to possibly date, but I wasn’t certain on that one either. #3 doesn’t count toward my assertiveness but serves as a warning for a lack of it. You can get in really bad situations if you go with the flow and the flow is not going in the direction you want. It might be flowing towards a giant waterfall. #4 I thought probably liked me, but boy did he do a good job hiding it. As his nearest & dearest female friend, I got to hear all about the girls he liked that were not me. Totally didn’t know how he would react, and took a greater chance at ruining the friendship than with #1, but you gotta do what you gotta do. If you don’t take chances, you might end up with Oops. #5 and I flirted in a friendly way but neither of us were interested in a long term commitment (haha!) at the time, so I really didn’t know what he would think of my intentions and if I was ruining our friendship all over again.
So, the moral is, take a chance. If you’re not already friends with the guy, what do you have to lose? If you are already friends, maybe he’s thinking the EXACT same thing but you’re both too shy to do anything about and and will spend your lives hopelessly dancing around the possibility that your friendship could be something more. And before you jump on me about being “too shy,” let me just tell you, you will never meet a shyer person than me. Seriously! I used to cry at the thought of talking to people. It was awful, and it was boring. Shy is a lot more work than just talking to people. Practice with your cats. Pick a few topics that you think people will respond to (suggestions: Lost, John & Kate Plus Eight, celebrity train wrecks, your favorite restaurant, whatever movies are playing at the time, 24, gas prices) and give it a try. Start with the checkout lady at the grocery store (just ask how her day is and BAM instant conversation) and work your way up. Don’t feel like you have to do all the talking. Hell, you dont have to do much talking at all if you find a chatty person.
Oh, but the REAL moral is, when you find your Keeper, CALL ME!! Have camera, will travel. Now get out there and put your best “I’m a hottie and you are incredibly lucky to have this conversation with me” face on. 🙂
