Another day, another batch of dating questions — some about losing hope in finding a partner, some about defining the relationship, and some about date planning. Perhaps one will especially resonate with you.

Q: We’ve been dating for three months. I’m ready to define the relationship. I'm afraid he might not be ready yet. Bring it up or wait a bit?

A: If you're always waiting, trying to guess somebody else's reaction, trying to make yourself more palatable for someone else's timeline, trying to put somebody else's feelings over yours, you will never get what you want.

Three months is a perfectly appropriate time to bring up defining the relationship. I know it's scary. You may be right that he's not ready, in which case he can tell you that and it's information you can use to decide what to do moving forward. Or you may get exactly what you want. But I would not live in the status quo for fear that you won't get the response you want.

Q: How to muster up hope when I’m feeling defeated?

A: I get some version of this question every week, and I’ve answered in various ways before:

-- Live your life "as if" — as if you aren't going to meet someone, as if this is the one life you get so you have to make the most of it.

-- Every day is the day before you might meet someone wonderful.

How I'm going to answer today is a little bit different.

I'm going to ask you to focus less on "hope" and more on practical steps for putting yourself out there. I want you to go through the motions — of going on the dating apps, of going to events in person, of truly being proactive about the dating process. That way, at least you know that you are giving yourself the best possible opportunity to meet someone. Hope in itself is not tangible.

I will also tell you that there are plenty of amazing people out there, but it often takes a lot of work to find them. I know that's not sexy. But it's the truth.

Q: What’s your opinion on dating someone who's not officially divorced yet but it's in progress?

A: Perhaps against popular opinion, I don't have strong opinions about it. Not all divorces are created equally, and sometimes the process can be drawn out longer than one wants it to be. (Depending on where you live and whether they have children, there are often laws as to how long you need to be legally separated before the divorce is allowed to go through.)

Ultimately, use your best judgment. Does this person seem available? Do they treat you well?

Are they fully past the relationship/living separately?

Only time can tell you those things. But no, I don't put a moratorium on people who are separated.

Q: We agreed to a date. How do I get him to take the lead on planning it without sounding entitled?

A: Try this: "Looking forward to it! I live in [your neighborhood/city/area] if that helps with planning and you have a spot in mind. I'm free Wednesday or Thursday if either works for you.”

Give someone all of the pieces to the puzzle, and then see if they are capable of putting the puzzle together. That way, you are essentially telling them to take the lead but also doing it in a collaborative way. Everybody wins. And of course, show your appreciation when they do choose something. A simple, "Thank you so much for picking a place!" goes much further than you may think. Positive reinforcement is a much better incentive than reprimanding somebody for not doing the exact behavior you want them to do.

Q: Six dates in, and we have the next planned — a sleepover. He's away and just updated his dating photos. Why?

A: I know it feels pretty crummy. He's still actively dating. That's what this tells you.

And/or that he got a nice new photo and wanted to show it and didn't think much about. But really, he's actively dating still. This is why I think it's a bad idea to continue to be matched with someone you're actively dating. Too much information and ability to stalk. Does this change your desire for the sleepover?

I agree that it's insensitive (if you're seeing someone regularly, don't update the profile) but not technically wrong.

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