How to Ask a Girl on a Date.

(This post has kind of exploded into many different ramblings, so I’m going to give you subheadings so you can skip to the sections that are most relevant to you)

Audience: Now, this works for a girl you have seen a few times, perhaps through mutual friends, a girl you talk to a few times at church/yoga/the gym, someone you work with (although I totally dated through the workplace one time and it turned out to be a bad, bad decision). It’s not necessarily the girl your friend is setting you up with on a blind date, because a casual coffee date is perfectly acceptable for that, since you both have NO idea if you will like each other, or the Prince of Nigeria who “wants to give you money” (don’t respond to him).

The Problem: “You know, now that I think of it, I don’t think I’ve ever officially been asked out on a date”, says many of my friends that I interviewed to write this post. How sad is it that many of us are now in our mid to late twenties–we’ve certainly gotten, “Do you wanna hang out?”, “Do you wanna Netflix and chill?”, “I’m getting off work soon…”–but yet we have never officially been asked, “Can I take you out on a date next Friday?”

I’m going to give guys the benefit of the doubt and just assume they don’t know how to officially ask a girl on a date, and have never been taught formally, which we can partially blame their mothers for, and partially blame social media for.

The cause of the problem: The other day, I was hanging out with a group of boys, and I was thinking about just how challenging it must be to raise a boy in today’s society (don’t get me wrong–girls certainly come with their fair share of challenges–I coach a team of them). With boys, there is a fine line you must balance, between giving your son love and adoration so that he feels cared for, and teaching your son to be a gentleman. I think, as women, we are tuned to dote on our men hand and foot–we want the world to be easy for them, we never want their feelings to be hurt due to rejection, we enjoy cleaning up after them–so we coddle them, and we don’t teach them how to be gentleman, and we never teach them how to ask a girl out on a date, because we always do the work for them. I’m totally guilty of this myself with my own brother. I just think he is so stinking cute and I love him so much that when it comes time for him to do his own laundry, I want to do it for him. When it comes time for him to do his dishes, I want to do it for him. When it comes time to pay for dinner, I foot the bill because I’d rather he cherish his hard earned cash.

The second culprit is social media. We grew up in a generation of AIMing (the reason I can type so quickly is because my parents would make my sister and I take 30 minutes intervals, so I had to type out everything I needed to say to my friends before the warning bell sounded and we had to switch). People are afraid of rejection, so if I ask a girl out via text message and she never responds, I can tell myself she never got my message, rather than dealing with those feelings of inadequacy and rejection.

Why it’s important to formally ask a girl on a date: There is a big difference between the guy I am dating, because I’m young, single, want to have fun and want to meet new people, and the kind of guy I’m going to marry. Certainly, the kind of guy I’m most attracted to is not the kind of guy that would work best in marriage; I could really like those fly by the seat of your pants kind of guys because they are fun and spontaneous, but when it comes time to be married, will he be able to sustain a job to support a family? Those guys who are the life of the party are really fun to be around, but does he require more emotional energy than I’m willing to give to a spouse? I might really appreciate a guy who buys me nice things, but then does he have expectations in return?

When you formally ask me on a date, it tells me two things: (a) that you have balls and (b) you respect me. In a guy that I marry, I really want to know that he has balls and that he is confident in his decisions. We will certainly confront situations with our jobs, our families, our children, our neighbors that I am going to need you to be assertive, and since I’m getting old, I need to see those qualities right off the bat. Also, I need to see that you respect me for all those standard reasons–I’m not an object, I don’t want to find myself in a domestic abuse situation, and if we have little Britany’s running around, I want to make sure you are respectful to me to teach her.

How to do it:

1.Do some research: You need to find some things out about the girl before you actually ask her out. First, you should probably find out if she is dating anyone. From a girl’s perspective, its super awkward to reject you because I’ve been with my boyfriend for multiple years and somehow, you never caught on. Next, you should find out a little about her–her likes, dislikes, what she does in her free time, where she comes from (I personally make it REAL easy for people, because my preferences and ideologies are splattered all over my blog, but chances are, the girl you are interested doesn’t have a blog). Thanks to social media, there are many avenues you can use to complete your research–be creative, think outside of the box. Her friends, family members are always a great starting point. It is a good idea to get these people on board as well, because inevitable what happens is, they want to talk about you, and the more they talk about you, the more excited she gets that someone is actually interested in her, and the more she ends up liking you. If you can find out a little bit about her–what her interests are, her schedule, what she’s looking for in a guy–and then tailor your approach, she’s more likely to say yes. I remember a guy telling me one time that he was interested in adopting a Rhodesian Ridgeback dog and I remember thinking, “Oh my gosh this guy is totally my type! How did he know I want a Rhodesian Ridgeback! There must be some ESP going on or something”–he obviously only said that because he did his research, but it made me like him more, and he certainly got the date.

2.Find a moment when it’s just the two of you: Perhaps you play on the same softball team, you throw a ball in the outfield for her to catch, you run up, and suavely ask her what she’s doing this weekend. Perhaps she comes into your store, and you find a brief moment to hold the door for her, and ask her if she would like to do dinner sometime. Perhaps you happen to catch her in the copy room, from your research, you know that she enjoys hiking, and you ask her if she wants to see St. Mary’s Glacier before the first snow fall. Or, you see her at a social gathering, wait for her to wander over to the crackling fire, and ask her if she likes Ed Sheeran. There’s two very important criteria about all of these gestures: (a) you are asking her in person, and (b) you are doing it privately, not in front of a bunch of people. By asking her in person, you are showing that you have balls, and by asking her privately, you are (a) creating an intimate moment, and (b) allowing her an opportunity to politely and privately decline (that respect factor). I mean, chances are that everyone around you already KNOWS what is happening because you have done your research, and they will certainly ask you about it afterwards, but giving her that moment away is so important (like Luke does in The Longest Ride).

3.Decide on a date that works best: Of course, you need to chat a little bit about finding a date that works best for both of you. By general rule of thumb, I’d say if you ask her out on a Monday, you could try to plan a date for Saturday, but if you ask her on a Wednesday or Thursday, you should plan the date for the following week (or, if you are thinking about asking me on a date, you probably need to schedule three weeks in advance). In managing people, I’ve found, what works best is to give them a couple options, and then expand upon those options if need be. So, you ask her, “Are you free next Saturday?”, and if she says, “No, I actually have a football game”, then you say, “How about Friday?”, and keep giving her options until you find one that works best for both of you. If she likes you enough (and isn’t in grad school/coaching a dance team in the middle of competition season), she will make sure she can make one of those options work.

4.Pick a time and place and tell her when you are picking her up: As women, we really need a guy to be assertive. Once you have decided upon a date, you need to say, “I have reservations at a restaurant–can I pick you up at 5 PM?” Or, “Traffic usually dies out in the later morning–can I see you at 11 AM?” Or, “I’ve always wanted to try swing dancing lessons–there’s a class downtown–can I come get you at 6 PM?”

And, be thoughtful in the location. It does not have to be anything uber romantic, especially for the first date, but I always think it is a little counter intuitive to take someone to the bar (where it’s SUPER loud and you come home with a hoarse voice and ringing ears from “trying to get to know someone” the whole night) or the movies (where you are staring at a blank screen the whole time and have no opportunity for conversation). I think its perfectly acceptable to ‘keep it a surprise’, but as girls, we like to dress for the occasion, so you just have to give me a little hint–am I wearing heels? hiking boots? do I need to shave my legs?…

5.Give her some space: I truly believe that absence makes the heart grow fonder, so once you have set a date, made plans, told her what to wear, give her some space. Likely, if I’m excited to go out with you, I’m spending my free time getting my nails done, my hair cut, buying a new outfit, telling all of my friends about you (which includes quite a bit of stalking). I think it is very appropriate to check in once or twice to tell her you are thinking of her and that you are excited for your excursion, but I personally get irritated when people contact me too often, because (a) it doesn’t give me time to miss you and (b) there’s a chance we could run out of conversation topics before the date even happens and (c) I appreciate you are respecting my time.  Plus, if we are getting married, we will have the rest of our lives to talk…

….then the date happens, and that’s fodder for another post, so just get yourself to the asking stage and we will go from there…

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