One of the biggest myths out there is that women need to sit back and be passive when it comes to dating. We have to wait for the men to find us, contact us. We have to sit and hope and pray for that man we’ve been pining over or for the man we recently crossed paths with to track us, hunt us down. During my single days, this constant passivity always felt terribly frustrating.

I recently received two emails from different women asking what they should do about a man they ran into.  Here they are (some minor details have been changed to protect anonymity):

Email #1:

“What are your thoughts on a situation where a woman asks a man to get together? I know all the “rules” say never pursue, but what do you feel as a LoveTrep? Last night I ran into a man I have had this amazing crush on for a year and a half. I was too shy to talk to him and he always tried with me. Well he ended up leaving the state for a while and we ended up connecting on FB. He confessed he had feelings towards me. However, with him leaving the area we just agreed that friends is good. I haven’t talked to him in several months. Last night I went to a Pilates class and you won’t believe who was there and smiled at me. HIM. We chatted and hugged. My heart was racing like it always does. We finished the class and briefly talked after. I hugged him again and said I will see you around. DOH. He asked if I would be back for the next Pliates class and I said I wasn’t able to. He knows how much I liked him and he shared he had liked me. Timing wasn’t right. I can’t help but think this isn’t coincidence. I don’t want to be passive in my love life, but I don’t want to be chasing some man. What would you do?”

Email #2:

Met a 45-year-old guy on a group bike trip.  Forgot my bag at a place we stopped 10 miles back.  He offered to bike with me up and back.  He told me he was divorced with 2 kids and told me why he was divorced.  He made me laugh along the way.  Asked me what I did and what I want to do.  We are both into health and nutrition.  Once I got my bag we had lunch at a nearby lake, his suggestion.  Once we got back, he wanted to know if I wanted to go swimming, but I declined.  We just said goodbye.  I would like to get in touch with him and through Google I can FB him as a friend request.  I’m not sure if I should do this due to the age difference (I’m 59) or if I should wait for him to find me or meet him at another bike trip.”

Both women were nervous about being the one to reach out first. The idea is this: “Well, if he’s interested, he’ll do anything he can to find me and reach out first.” While this may be true for some men—particularly dominant, super confident, Alpha-type men—and, surely, many men have been socialized to know that it’s their “job” to ask out the woman, I do believe that many men either need the nudge or appreciate hearing from a woman first to know that it’s OK to take the next step with her. It’s the equivalent to giving a guy a signal in a bar, through sustained eye contact and a smile, that it’s OK to approach. Oftentimes, men need those signals, maybe more so today than ever before.

These women were willing to let a perfectly nice opportunity to make a new connection pass them by because of some strict adherence to “rules” about what a woman should and should not do. In both examples, the men had given some indication that there was or might be interest, so why not follow up in a fun, lighthearted, eezy-breezy kind of way? Maybe the men in these scenarios didn’t take the reins because they got sidetracked or had a family emergency or weren’t sure of the woman’s interest to begin with?

In both cases, I advised both women to go for it.

To the bike woman I wrote: When you look back on your love story when you’re old and grey, do you want your story to be one of fear, hesitancy, and doubt, or do you want it to be one of risk-taking, vulnerability, and empowerment? You’ll never know what he was thinking by just sitting and waiting to run into him again, if that ever happens. You could send him a cute little note after he accepts your request: “Thought I might find you on here. (Insert joke or shared reference about your bike trip). I’m going on another trip in a few weekends. (Insert what trip it is). Maybe I will see you there!” See how he responds. You’ll soon find out about his interest level.

To the Pilates woman I wrote: I say absolutely message him on FB! Carpe diem, girl. Forget the passive BS that says never pursue. Every situation is different. There’s a time to sit back and let the guy ask you and a time to extend a friendly offer. I’m sure he’d love to hear from you. How about a quick FB message that says: “Hey stranger, it was great to see you the other night! Would love to get together for a drink one night and catch up.” If he’s turned off by a friendly invitation like that, well, is that someone you want to be with, anyway?

Because really, what did they have to lose? If a woman reaching out to say hello or to make a connection electronically is enough to turn a guy off, is that really the type of guy you want to be with, someone who feels emasculated by a friendly email or invitation?

I asked my now-husband out for a drink via; a close friend of mine made the first move with her now husband by asking him to grab a burger and a beer after work. There are loads of other love stories I’ve heard about in which women threw out the dating script.

While general guidelines can be helpful sometimes for certain people and in certain situations, don’t be so glued to dating “rules” that you don’t ever take risks.

Life’s too short to always play it safe.

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