Single Career Girl: Should You Make the First Move?

Posted January 5, 2013 by Marcy Farrey in Life After Five

There’s a guy you really like, and you think he likes you — he’s always talking to you, asking what you’re up to, maybe even emailing or texting you. But he’s not making a move. He’s not asking you out.

I’ve been here many times before. I consult friends for advice. Do I just ask him out? Most say that times have changed, and you can certainly make the first move. A woman doesn’t have to wait anymore, and a guy can be just as nervous as you are.

I am a girl that has taken that risk. Even when I was in middle school, I tried to ask out all of the boys I thought were cute. I humiliated myself — a lot — and I eventually learned my lesson. In college and in my early twenties though, I once again tried to make the first move. Sometimes I’d be fairly certain a guy was in to me, and as soon as I asked if he wanted to grab coffee or a drink, he’d back off. Other times, it really worked out, and I ended up dating the guy for quite awhile. I figured it was hit or miss, and all a part of putting yourself out there.

Lately, I’ve been debating whether this is the best thing to do — I wonder if asking the guy out first is where I’ve gone wrong. My attitude has changed from adventurous to cautious. I sit back and think, “If this guy is really, truly into me, he’ll find a way to make sure I’m his.” And do I really want to date a guy who isn’t confident enough to make the first move? I look back on a past relationship in which I made the first move — and I later discovered he was holding back because he wasn’t sure he was ready to ask me out. He needed to get certain things in his life in order. And the fact that he didn’t have these things in order was one of the reasons we eventually broke up.

I’ve talked to a few single friends about this, and one of them told me that most of the time, she’s had to make the first move. She’s now in a happy relationship with a man that she finally turned to and said, “Will you just ask me out on a date already?”

Regardless of whether these relationships ultimately work out, what I have learned in this process is that it’s more than okay to make the first move. You just have to accept the risk that comes with putting yourself out there, and if it doesn’t work out, be proud of yourself for your bravery! Perhaps the problem is not in whether or not we ask first, but in who we choose.

I’m curious to hear what my fellow Career Girls have experienced. Have you ever asked out a man first, and if so, were you happy that you took the risk? Did it work out? Send me an email or respond in our comments section!


About the Author

Marcy Farrey

Marcy Farrey is a videographer, writer, and editor. In her previous life, she worked as a broadcast news reporter and producer in Lincoln, Nebraska and as a writer and producer in Minneapolis, Minnesota. She has a Master of Arts in Writing and Publishing from DePaul University and a Bachelor of Science in Journalism from Northwestern University. Learn more about Marcy on her website

One Comment


    This is something I have been debating with lately as well! It’s worked for me in the past (in fact I may have made the first move recently haha) but I always wonder later on if it was the right thing to do. Great post!

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