I really like this guy but I’m scared to ask him out. Just go for it, says our elder. You’ll kick yourself if you don’t.

Dear EWC

So, I have liked this guy for about a year and a half. He is so sweet and funny. He’s in a band. Just the typical stuff. The thing is he is best friends with my best friend’s husband. I asked about him once and they mentioned that he was single and looking. The other thing is that we are both 25 and never dated anyone. We are both shy. I have weighed the options in my head and I just can’t bring myself to message him. I keep telling myself that if he was even a little interested he probably would have asked me out by now. But what if he is like me and just can’t ask me out? Also what if I do ask him out and he says no? Then I’ll have to still be around him a few times a year. And I also don’t want him to like say anything to our mutual friends about how weird I am for asking him out. It could go alright and we could actually end up together. On the other hand we could be alright and end up together. I’m just afraid that he will not return the feeling. I am struggling. I feel like I am way too old to feel like this and not just ask him out. I feel stupid.

Phil replies

I have some ideas on your questions. I hope you will consider what I have to say.

Believe it, or not, almost everyone experiences difficulty when asking someone to go out. Not just the shy people but most everyone else. The thing is once you do it it becomes easier and easier. You find out that the other person isn’t waiting to call you “weird” or anything but maybe is yearning for your call.

I always put it this way when considering whether to go ahead or not: “What is the worst thing that can happen if I call and if I don’t call?”

If I call and he says “no” I am disappointed and hopefully will get a second chance. If I don’t call I will always be wondering the same things that you are now. What if ? What if?

In my life, I have found one thing to be absolute. I have never regretted making a move towards dating or business or almost anything. I have kicked myself a thousand times for something I didn’t do. So, yes, I am suggesting that you go ahead. Time is wasting.

It needn’t be anything tricky, just, “Hey, let’s have coffee one of these days.” See, no pressure on you or him, and you will have a major opportunity to begin a dialogue with him. Do it now, don’t wait, you will never be sorry you did.

Letter #: 453005
Category: Dating/Relationship