As always, dating can sometimes feel like a conglomeration of awkward situations, ones we have no idea how to deal with.

I stand by my advice that I give often: I don’t want you to be scared of talking to the very person you supposedly like so much. If they’re a true partner, it will feel like a safe landing place for your concerns and requests.

Question: We’ve been dating for four months. His house is a mess! How do I gently tell him that I can’t handle it? I’m a 52-year-old woman, he’s a 57-year-old man.

Answer: Here’s what I recommend saying: “May I ask you something awkward?”

He will, of course, say yes. I find that starting conversations like this often diffuses situations so you feel more comfortable saying the thing you want to say.

Then so on to ask, “Have you ever considered a cleaning service? I find that it really helps me with stress and peace of mind.”

Relating it back to you makes it less of a judgment. Assuming he has follow-up questions, you can get into the fact that you noticed whatever you did.

Question: The person I'm dating asked me to come see their stand-up. What do I do if they're not funny?

Answer: First of all, before you start panicking, let’s be happy that the person you’re dating wants to let you into an important part of their lives. That’s a win!

Now back to your question: What if it’s not funny? I truly believe that you do have to respect the person you’re dating. And so you not finding them funny in something that they are clearly passionate about is hard to get over. Ask yourself this:

Is it just a difference in sense of humor, or a value mismatch?

Did you find it offensive?

Do they have a day job?

Are they just beginning?

Do they have a different persona on stage than they do with you?

It’s OK to not love everything your partner does, so I would bring it back to the respect thing.

Question: Is it a bad sign if he is messaging constantly throughout the day?

Answer: If you are answering every text and not indicating that you don’t like this behavior, then, in the nicest way, I actually blame you for it! (Some people love texting all day. Though I will say that texting is not dating.)

You can simply say, “I appreciate you thinking of me, but I can’t text that much during the day. Thanks for understanding!”

Then, if he continues to blow up your phone, we know he can’t uphold/respect that boundary. But until then, he’s just doing what he thinks you like.

Question: How do I stop being anxious about a new relationship? I feel like I’m always waiting for the other shoe to drop.

Answer: I’ve had two clients do this in the last week: Make a list of facts. Facts may include how your last conversation went, how often you see each other, when they last reached out to you, how you feel in their presence, etc. Only things that actually exist. I’m guessing you’ll like what you see. Then, on the other side of the page, make a list of stories. Ones you’ve made up. Look at the difference. Facts are all we go on.

My last piece of advice here is not to doubt everything they say to you. Not to doubt their love. Not to doubt their affection. It’s too exhausting for the person you’re dating to continuously try to prove themselves to you, that they truly want to be there. Don’t make it become a self-fulfilling prophecy by not believing it can be real.

And also, if nothing has changed, then nothing has changed.

Question: How do I get over someone I dated for 2 months? I’m embarrassed that I’m still sad!

Answer: You’re allowed to feel sad. That’s normal. Sometimes the shorter ones take longer to move on from because it’s the lost potential we need to mourn the most. The relationship that could have been. But we need to remember that everything we’ve built up in our heads (and, of course, we only build the positive in our head) probably would never have become the reality. I know that doesn’t make it easier.

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