A new batch of questions, and a new batch of answers!

Q: When is it time to ask about how long someone has been single and whether they have been married before? In person or still in the app before meeting?

A: I have a question for you: What are you hoping to garner from this information? Is there a "right" amount of time for someone to have been single? A month? A year? Five years?

I understand that everyone is trying to assess people quickly and efficiently, but I strongly recommend staying away from questions about people's past, certainly before meeting and also on the first few dates, because hopefully their past helped them become who they are now.

Trust that things will come out if they are going to come out. You will know if someone is not ready by how they treat you. You will know if someone has bad feelings about an ex by how they speak of them, unprompted.

I fear that asking these questions to try to weed somebody out will actually weed you out because it may seem off-putting and premature, which sometimes comes off as un-self-aware.

And you will probably get different advice from friends or other dating coaches. That's OK. This is just what I recommend.

Q: How to get over a breakup? My heart hurts.

A: I know this feeling. Sadly, most of us know this feeling. And yes, it does feel like your heart hurts. Because it does. I wish I had magic words to give you. I wish I could tell you to take a pill to make it go away. But I don't. And I can't.

As a former therapist told me a long time ago, the only way out is through. These things take time. Often, more time than we want. The best advice I have is to revisit yourself and who you are. Spend time with friends and people who love you. Reconnect with hobbies of yours that you let go when you were in the relationship. Buy new clothes and things to express who you are today. These things are not to mask hurt. But they are to bring you back to who you truly are.

I don't have a magic answer. But what I can tell you is that you will get through this. And you will come out the other side stronger. It doesn't feel like it now, but gradually, it will. I promise.

Q: After a month of non-exclusively dating, I noticed he updated his profile. Is this a sign that he's moving on?

A: This is why it's so weird to continue to be matched on a dating site while you are actively dating this person. But anyway...

I don't have the answer to your question. If you've been non-exclusively dating someone for a month and they update their profile, does that mean they are moving on? I would say no. I think it means that they are still looking, though. And that they probably got a new, cute picture of themselves and wanted to share it and honestly didn't think about how it might impact you. (You would also be asking me this question if he unmatched you.)

If you're upset by this, which I'm guessing you are (and which isn't totally unreasonable!), it's worth talking to the person you're seeing. Might you want to bring up exclusivity? Or at least unmatch each other so that you're not obsessing over their profile? All options. At the very minimum, it's probably worth talking about what you are each looking for if you haven't already.

Q: How to manage the grief associated with not finding what you're looking for?

A: This is an interesting question that I can answer in a few different ways.

First, I completely understand what you're saying. Most people's lives don't go exactly the way they want. So we do have to mourn the loss of our vision. That's a real thing.

Next, I truly want you to evaluate what you're looking for. Because what if what you're looking for is so narrowly defined that you're making it harder to be happy? Or to find it? Without knowing any specifics, that's all I could really say on that.

And lastly, the way you're asking seems like a forgone conclusion. Just because you have not found what you're looking for yet does not mean you will not find it, whatever that is. Every day is the day before you might meet someone incredible. So be open to that possibility.

I hope this helps!

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