Is V-Day too soon? 

I want to ask my crush to a movie. Is it weird to do that a week before Valentine’s Day? 

The most important thing is to be yourself, says our elder. Ask him when it feels right to you.


Dear EWC

My mom recently found out about my crush, and has been asking all these questions about him. I’m alright with her asking. She recently asked me, “Why don’t you ask him to a movie sometime?” At first, I basically thought that was ridiculous since he still left the liking on a “I don’t know”. I’ve thought about it more and I think I will ask him. If he accepts the invite to the movie then it could move into something else, if he declines then I fully know that it’s time to move on. If we do, however, go to the movies, what kind of conversations should I start while waiting for the movie to start? I’ve thought about asking him if he likes our school – he’s only been here for a school year and a half. I don’t really know what to say or ask. The other thing is, would it be weird if I asked him a week before Valentine’s Day? I don’t really want it to correspond with V-Day.


Grandpa-Matt replies

A good strategy is to ask open ended questions. Not something that can be answered with one word, like fine, OK, cool, etc. An open-ended question might be like asking him to describe something, or his opinion about something. And then keep asking the follow-up questions. For example, instead of asking if he likes our school, it is better to ask what are the things he likes (or doesn’t like) about the school.

The truth is that most people like to talk about themselves, while effective communications are best handled as a two-way street, with a lot of give and take happening, a person who seems interested in another is usually thought of as an interesting person themselves.

Honesty and being authentic will require you on occasion to talk about your personal life. As long as you don’t go into a lot of drama, and speak as you are the victim of others, you will do fine. A good rule is not to complain to anyone that can’t do anything about the situation.

Attempt to avoid asking for advice at a time that you are unwilling to take it. This will allow you to steer away from going into depth regarding personal problems. I recommend a website that can help you make better conversations.  and

 I think that it takes practice to be good at it. Don’t be discouraged if it is not excellent in the beginning. Keep at it and it will eventually work for you.

The best advice that I can offer you is to be yourself when speaking with him. It is the authentic you that he is attracted to. Often, we try too hard to sell ourselves. Sometimes we try to guess what the other person wants to hear and then try to present ourselves in such a way to match what we imagine that the other person wants to see. In such a case we often lose what has attracted the person to us in the first place. 

About when to ask him, any time is a good time to ask if the situation works for you. If you want to avoid the V-Day thing, it is for a reason. Maybe you don’t want to make it look like a bigger deal than it is for the first date. Maybe you don’t want him to get the idea that you are pressing him to become a couple. I don’t know what it is, but I respect your position in this matter. If it were me, I’d consult Mom because she has your interests at heart and has her teenage experiences to rely on.

Article #: 418421

Category: Dating/Relationship

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