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THE QUESTION

How long should one person wait for another to be ready for a relationship? Being gay makes this all the more challenging. After meeting in December, it seemed all was right. However, he has a lot of damage from an ex. Part of me feels like I owe it to him to wait because I don't want to pass this one by. However, waiting is also something I'm not good at. We've had a heart-to-heart where he clearly wants to be more with me when he's ready. I want more with him when he's ready. I also am worried about meeting someone along the way, while I wait. What do you think? Should I wait or move on?

THE ANSWER

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Two things I've always felt are crucial in the early going of – or, I guess, in your case, the roll-up to – a relationship: momentum, and exclusivity.

Now, bear in mind this is just one man's opinion, and an old-fashioned man at that.

I am aware that many people these days (okay, yes, millennials, I'm looking at you, a bit) seem content to lurk in the grey area between "hanging out" and "hooking up," who love to pay late-night visits to their "friends with benefits" on the booty-call side of town, and, even while on a first date with someone, are swiping through apps on their phones looking for fresh prospects.

But I don't like the sounds of any of it! I would go so far as to say I don't believe in it.

What I believe: When, after wandering lonely as a cloud in the wilderness of singledom, you finally spot someone you're interested in – when, as they say in the military, "the target has been acquired" – knock back a glass of chardonnay, or (better) a shot of tequila, and cha-a-a-rge! Go strong to the hoop, in other words. To mix sports metaphors: How else are you going to punch above your weight?

I went strong to the hoop, and notoriously punched above my weight – to the point where people will come up to my wife (with me standing right there) and say, their faces alight with "sociological interest": "Pam, when you first started going out with Dave, what did you see in him, exactly? No offence, Dave."

She uses these occasions as a bully pulpit to issue a statement to bachelors and bachelorettes everywhere: "There was a lot I liked about Dave. I'll tell you one thing, though: I was never in any doubt he was interested in me."

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He/she who has ears, let him/her hear.

In your case, I get no real sense of momentum or exclusivity – or even interest, particularly. Where is his fear of losing you, for example, of letting you slip through his fingers because of his ambivalence and wishy-washiness?

In my experience, saying "I'm too haunted/damaged by my ex to be in a relationship right now" tends to be code for: a) "I'm not that into you," or b) "I'm kind of waiting for someone better to come along."

Of course, I don't know you, or him, and I'd be an irresponsible advice columnist if I didn't insert a caveat here that maybe he is just really hurt and damaged and not ready. You have to make that call.

But sounds to me like he's stringing you along. If he were really into you, I can't help but feel he would set aside all his "haunted" and "damaged" feelings and allow you, Dr. Love, to heal him with the power of your affection.

That's what I'd do. After all, what's better for healing a broken heart than a fresh relationship?

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I think what you need to do here is: a) throw down; b) back off.

By "throw down," I mean tell him, in no uncertain terms, how you feel. I don't mean to put words in your mouth, but maybe something like: "Listen, I really like you and want to be with you. I figure you're either into me or you're not. If you are, I really think we should make this happen – and sooner rather than later. If not, the only right thing to do is cut me loose so I can find someone who is."

(You might get your heart broken at this point, but hey, better broken than slowly unravelled.)

And then back off, by which I mean stop pursuing him and "being there" for him and go out and find someone who will take one look at you and say: "Yes! I'm all in!"

Of course, at that point, "Mr. Maybe" may come after you. That's human nature (for some people).

By which time, of course, you might be happily unavailable. But that's the risk he's taking, and I think deep down, he knows that.

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Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.

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