Asking out a Shy Guy

Ask Deb –

My name is Maali. I’m 22 and a few months ago I met this guy who happens to be my little nephew’s swimming coach. Well, I have to admit that I liked him since the first moment I saw him, but I really didn’t think that anything could happen between us, since he’s sooooo shy and serious. With time, he started paying more attention to me and giving me flirtatious looks, but when our eyes meet or when we come, close he blushes and says “hey” nervously.

So I took the initiative and asked him a random question just to break the ice and see what happens and, to my surprise, he seemed to be very happy with me talking to him and he came and sat by my side and was talking and smiling and looking at me straight in the eyes and we exchanged phone numbers; but he never called.

So I took the initiative again and sent him a message, just asking how he was doing. He texted me back then gave me a missed call, then texted me again and said that he liked my ringtone. Yet when we met face to face after that, he was so nervous as if he did something wrong, but he kept on looking and smiling as usual and being friendly (saying hi and walking me and my sister and her son to the car).

The thing is, he wants to talk to me as he always sits by my side when he sees me but he doesn’t say anything more than the usual hi and how are you doing. He became a very good friend with my sister (he knows her for more than a year but never talked to her until I started going to the pool). She once asked him in front of me about a ring he was wearing in his left hand and answered that it was a gift from his sister and said that he was not engaged in any kind of relationship and looked at me as if I were the one who asked the question.

Well, yesterday he came and talked to me then he asked me if I read the announcement about the holiday they are going to take next week. But I really dunno why he asked me that question!!!! Later, he offered to give my nephew a ride home and he did and everything was going very well until I texted him just asking him how was the ride with my nephew and told him that he liked it a lot but he never answered!

The thing is he is very well mannered. He never ignores me and I was shocked not hearing from him. I really want to understand this guy: does he like me or not? Should i go through with this thing or back off, as i’m starting to fall for him.

Is it that difficult to get him to ask me out or what? Please help!!!

Dear Maali –

When you have a guy too shy to make the first move, you’re going to have to make the first move yourself. Luckily, we’re in the 21st century, so that’s no problem, unless you have a personal preference for men who make the first move. If you’re okay with asking a guy out yourself, here’s how you do it.

It sounds like you have taken several of the first steps, so this should be easy. Well, as easy as it ever is to make a connection with people.

1. Location Is Everything

When you want to ask someone out, you’ll want to do it when you have their undivided attention and they aren’t busy with something else. It sounds like the two of you have plenty of “alone time”, so you should have no trouble picking your spot.

2. Make Small Talk

Once again, make small talk with your guy. Make a pleasant comment about something he’s wearing or something he does. See how he handles a compliment. This also gives him a signal you like him and you’re interested in him.

Now that you have his attention, mix in three other elements to your conversation: eye contact, flirting and questions about him. All three of these sends signals you’re interested, while not committing you to anything, in case he doesn’t respond well.

3. Make Eye Contact

Eye contact does two things for you. One, it gives him a further indication you are interested. Two, it gives you a chance to read his eyes. The eyes are the windows to the soul. You should get a pretty good idea from his eye contact what he thinks of you.

The next time the two of you look at each other, maintain eye contact just a little longer than you normally do. I’m not talking about staring at him or being creepy, but holding his gaze an extra second or two.

Notice what he does. If he makes eye contact back, he’s more than likely interested in you.

4. Flirt A Little

Most people know how to flirt, but are just out of practice. One of the first things children learn to do is playfully flirt with people. Unfortunately, that instinct is taken out of us at an early age. You know how to do to be playful and flirtatious, even if you don’t do it all the time.

Laugh at any jokes he might make, whether they are intentional or not. Be playful. Touch him lightly on the arm. Give him a compliment or two, but not too many. There are subtle and not-so-subtle signals you can give him that you’re interested in him.

Test his reaction to these. If he flirts back, you’re on the right track.

5. Quiz Him

Ask him some questions about himself and gauge his reaction. Ask him what he likes to do for fun. Ask him what sports (besides swimming) he enjoys. Ask him what food he enjoys. Ask him what he does on the weekends, or what he does with his friends.

Once again, these do several things for you. It shows you’re interested. Two, it gets him to talking. You give him an opportunity to open up, because people know themselves best and will talk about their likes and dislikes more than anything else, even if they edit out information they don’t want you to know.

Also, you might be able to find out more about him. Once you start to learn about his likes and dislikes, you’re going to start to see him for who he is.

Of course, your questions also get to the overriding question: what about that ring on the finger? It’s probably just as he says, but keep it in the back of your mind if any of his answers sound suspicious. There’s that outside chance he likes you, but he has another relationship he doesn’t want to talk about. Don’t assume that’s the case, but don’t get blindsided by it, if that happens to be true.

6. Ask Him Out

Given that you’ve known this guy for months and the two of you have had lots of time together, you may already be at this point. If so, skip to the “asking him out” point.

By this point, you should know enough about the man you’re interested in to know some things he likes to do. Find some activity you also enjoy and ask him to do it with you sometime. If he likes scary movies and you like scary movies, ask him to go watch a scary movie with you. If he likes sushi and you like sushi, ask him out to a sushi restaurant. If he enjoys riding a bike and you enjoy riding a bike, ask him to go bike riding.

Anything works, as long as you both enjoy it. This will put both of you in the best light, instead of one suffering through an activity just to be on a date. Also, if he turns you down, it’s likely that it’s not because he doesn’t like what you ask him to do, but he doesn’t want to do it with you. (The timing might be wrong, so don’t be entirely devestated. If he shuts you down categorically or turns you down several times, that’s a hint.)

Whatever the case, at that point, he knows you’re interested. Whatever shyness or hesitations he has should go by the wayside, because most shyness has to do with lack of confidence the other person will be interested. Once that’s out of the way, a shy guy tends to just be a guy.

Asking Out the Shy Guy

Hopefully, that will do the trick. Remember, if you ask a guy out, be prepared to pay for the date. If he insists on paying or going halfsies, don’t make a big deal out of it. Just a heads-up to be prepared to fund the nights events.

Good Luck,
John Clifton