Online Dating Blog

For me, online dating was a godsend: I always had trouble approaching women in day-to-day life. For example, if I’m remembering correctly, I only got two phone numbers at a bar in my life prior to online dating (and one of those only applies if Applebee’s counts as a bar). It was always something I overthought and the benefits of online dating propelled my ability to find and connect with people.

If you’ve read my guide, you know that after I started dating online I did get much more comfortable approaching women (it had reached a point where rejection didn’t matter because I had so many opportunities). Still, even with that success, I hesitate on giving advice when people contact me about talking to women “offline” because I always end up feeling a bit hypocritical if I tell them they are overthinking things or tell them they just need to talk to her.

I know personally that doing so is harder than it sounds.

At any rate, I received the following email from a reader last week:

Talking to the Woman You See Every Day But Don’t Know

So my hypocritical answer is to just go talk to her. In this case, if the only thing holding him back is the jogging attire it seems that taking a morning walk in nicer clothes could solve the problem.

But just walking by in clothes may not give him the opportunity he’s hoping for to actually talk with her so here’s what I ended up suggesting:

1. Determine when the bus at the bus stop arrives
2. Go to the bus stop early (in nicer clothes!)
3. Strike up a conversation. This shouldn’t be too difficult since he’ll have time to plan and he sees her every day.
4. When the bus comes, there are a few options. First, if things are going great conversation-wise, I think he could just fess up and admit he didn’t need to ride the bus but wanted an excuse to talk to her and ask for her number. Alternately, if the timing of the bus gives him no time to talk with her, he could find a reason to ride the bus and try to keep the conversation going there.

Now every situation is different but I think one benefit to approaching the woman you see every day (but don’t know) is that you can do some planning.

Ladies: Is This Overthinking Things?

I’m interested to see if women think that my advice was overthinking things so your feedback is welcome. I know plenty of people will say that it is – that he should just stop while he’s running, panting, sweaty, and start a conversation with her.

However, as a man who has struggled with the “just walk up and talk to her” approach myself, I honestly don’t think that feedback is helpful in many cases. For some guys, having an excuse to talk in a more planned way will make the difference between success and failure.

That being said, I’d love to know what you think!