6 Questions That Go Through His Head Before He Asks You Out

Once a girl gives me her number and agrees that "we should go out sometime," things get all complicated.

Once a girl gives me her number and agrees that "we should go out sometime," things get all complicated. Perhaps I'm guilty of overthinking, but there are many wrong turns I can make as I try to get to my ultimate destination: a date.

I sort through many questions in my head about the best protocol for setting up a date. You'd think that if a girl says she's interested in going out and gives me her number, then it's a done deal. You'd be surprised how many people, when put on the spot, might say something just to be nice. In other words, there are no guarantees.

The usual rules I've put on myself hold true for the first-date process:

Here are the questions I ask myself as I'm trying to set up a first date:

How long do I wait to actually ask her out?

I try to wait until two days before the date to make contact. So, if I get her number on a Saturday night, I target the next Thursday as the date day, and contact her Tuesday. But it's certainly possible to wait too long to contact a girl, just like it's possible to attack the next day and look all psycho and overanxious.

Great. I have her number, but should I call or text?

Women seem conflicted on this question. Texting seems much more casual, and who even talks on the phone anyway? But some women tell me that it's nice for a guy to actually pick up the phone and call her to ask her out.

I'm the one who suggested we go out, so should I have something in mind already?

I always thought it was nice to leave it open for discussion. It's gentle and allows the woman to have an equal say in what we do. But many women complain to me that guys ask them out and then have no idea what to do on the date.

Should I do something offbeat and cool, or do the standard dinner and drinks?

I hate doing the "Want to get a drink after work?" or "Want to grab dinner?" but it's the safest approach. There are awesome things to do: rock climbing, taking walks, going to sporting events, going to shows, etc., but that might be tough on people who don't know each other. Maybe it's best to ease into it with a few "standard" dates at first before you do the big stuff.

I've had mixed results — women tend to love to go to sporting events, but (in my experience) sports dates haven't turned out too well. And at shows/movies, it's just hard to talk.

Should I go expensive or economy?

Another thing about getting tickets is that it's obvious that I've spent a lot of money, and that can be overwhelming to a girl on a first date. The same thing can happen when you go to an expensive dinner or keep buying expensive drinks — someone might think: "Why is this guy buying me so much stuff?"

On the other hand, if you go too cheap, that's noticeable too. But it looks more casual and isn't so overwhelming. I guess it's better to go not so expensive on a first date, as long as it's not fast-food cheap. Although, if a girl took me to Chick-fil-A on a first date, I'd want to marry her.

Do I suggest a weekend or weekday?

It's tough to hijack someone's weekend with a first date. Weekends make it less casual, and people aren't always willing to give up their Fridays and Saturdays to someone they don't know too well. Again, the safest bet is to do baby steps, I think — suggest something after work. That way, you both have the excuse that you have to get up early for work the next day in case anything sucks.

Perhaps I've been dealing with the wrong girls. Maybe my process for setting up a first date (as long as it's not totally weird) doesn't matter if I'm dealing with a nice girl. But it's a shame that incorrect "protocol" for setting up a date can doom something before it even has a chance to start.

What are your thoughts on my questions above?

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