I've been having trouble asking out a particular girl I know. I am confident enough to approach her, but I can't seem to bring myself to pop the “date” question.

Do you have any advice on how I can bring myself to ask her?

Delayed Action

You’re probably doing better at it than you think. You’re already approaching her, so you’re talking to her about something. Since you’re confident, she must be responding. That’s a decent start towards your goal.

For your next approach – find some common ground to talk about, based on how you know each other, e.g. work, school, community, friends, etc.

From that conversation – then or even on another occasion – have some idea about what you two would likely enjoy together, e.g. a more specific chat over coffee, a movie, an event coming up, etc.

That’s when you’ll ask if she’d like to do this together. If the time/place isn’t right for her, be flexible.

If she asks, “is this a date,” say that’s what you had in mind. It gives her the chance to reveal if she’s actually attached and you weren’t aware of it, so that you know early on and don’t take it personally.

I’m almost 20, and have been in a relationship with this guy since I was 16.

I need advice on what to do, whether I should let go or hold on.

We’ve been through a lot and I’ve cheated on him. But I have been faithful since. And we sorted out our communication issues.

Our relationship is very on and off.

We’re good for a while, then this weird tension will often occur, and we break up or get into dumb fights.

We decided that we should not continue this relationship but now he wants me back. I don't know if I should get back with him or if I just need to move on.

We both seem to want different things but we also have a lot in common and when we are doing well, we get along great.

Is this relationship right or not?

Weird Tensions in New York

Mostly, your relationship sounds typical for your age and life experience. It’s not “weird,” but it’s also not seasoned and ready for a long-term involvement.

A defined break would be healthy for both of you. Dating others and getting to know others (not just running from one person to another) will help you assess each other better as boyfriend and girlfriend.

For example, just because you have some things in common, does NOT mean you’d expect to have the same goals. Yet, at this stage of life for both of you, goals are important.

One of you may have dreams that require more years of education, while the other may not have interest in that, and be satisfied with his/her current status. It’s unlikely a couple could stay together if each already has such different hopes and plans for the future.

You won’t know if this relationship is “right” for you unless you look at such things, as part of the big picture about your guy.

The “on and off” has happened so far because of your youth and inexperience with commitment, but also because you haven’t looked beyond the present.

A six-month break (no dating each other, no sex together) will give you both time to look back, reflect on what caused the tensions and fights, and look forward to where you want to be in five years – with him, or not?

FEEDBACK Regarding the girl, 17, who’s graduating high school and whose parents are pressuring her (April 28):

Reader – “She needs to have someone speak to her parents because it's obvious that they don't listen to her. I’m concerned because she appears to be feeling trapped and doesn't know what to do.

“She’s staying in her room “rather than talk to them” and that can lead to deeper depression or cause her to seek a desperate solution.”

Been There

Ellie – Unless the relationship has been abusive, I believe parents are the first go-to resource for young people to open up about their anxieties, in order to lessen the pressure they feel.

However, I respect your experience and agree that if she feels she cannot do that, she should talk to a school counselor, a respected teacher, principal, or faith leader if available, to help her parents understand what she’s feeling.