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Welcome back to Mostly Dating, a newsletter designed to help you transform your dating life and relationships.

I am SO excited to be back. This era of the Mostly Dating newsletter is going to be better than ever. Every Friday, we’ll dive deeper into reader questions and various dating, relationship, and self-care tips.

Want to be suggest a topic or submit a question (anonymously) for a future send? Send me an email here.

Conversation starters for better dates

Two of the biggest things I see people struggling with on early dates are what to talk about and how to make it feel conversational (not like a “job interview”).

And the truth is: Even if you and your date have amazing chemistry and are super compatible, it’s normal to freeze up sometimes—or to experience lulls in the conversation.

The trick is having a few topics/techniques to rely on when those silences do (inevitably) happen.

That’s why I developed my 6 fool-proof conversation starters (& savers):

🤍 1. relate to them: Use what you do know about the person to build a conversation and create a bond.

Ex. any shared interest, destination you’ve both traveled, where you’re from, etc.

🤍 2. use the setting: This one is so easy and can spark great conversations. Literally look around and comment on something that catches your eye.

Ex. “Wow I didn’t know this place had a backyard! I’m always looking for outdoor spots, what are some of your favorites?”

🤍 3. ask for recommendations: On that note, people love sharing recommendations. Plus, it shows you value their taste/opinion.

Ex. “I’m really on a burger kick lately, what’s your favorite burger in the area?” or ask for recs for movies, books, shows, travel, etc.

🤍 4. the “teach me something”: Show you’re interested and impressed by asking questions about a topic they seem to know a lot about. Learning new information can help build connection, and people feel good when they teach someone something new.

Ex. “That’s so cool you’re fluent in Spanish. Teach me a phrase!”

🤍 5. give a compliment: Research shows a correlation between compliments and greater relationship satisfaction.

Ex. “That’s a really cool jacket, where did you get it?” or “You have great taste in restaurants. How did you find this place?”

*I have a post with specific compliments to give on early dates & why you should!

🤍 6. the “about them”: Another thing that makes people feel good? Talking about themselves! It should be a give and take, but asking an open-ended question about them is a great way to start a well-flowing conversation.

Ex. “I loved all the travel photos on your profile, what’s the top trip on your bucket list?”

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Research-backed tips to make someone like you

Important clarification: This is not about tricking someone into liking you, or acting like someone else in order to get their interest. In fact, it’s the opposite.

Here are a few research-backed ways to make the right person like you more:

• mirror their behavior (don’t overdo this one!)

• use their name in conversation (don’t overdo this one!)

• show your flaws (people are attracted to imperfection, uniqueness, and humanness!)

• do an activity together (*I have so many posts with activity date ideas!)

• share something personal (don’t overdo this one!)

• smile and make eye contact (more than you think you need to!)

• graze their arm, leg, or back (if you’re feeling the vibe)

• compliment them (again, check out my post with compliments to give!)

• be a good listener (ask follow up questions, nod along, etc.)

• be yourself (!!!) 

Reader Q&A:

I’m curious if he said this to on the date or if you guys texted after the date and he said it then. While I hate to say this, I truly never put too much weight on what people say on the first date about future dates.

And that’s not at all to say you won’t hear from him! I just think many times people either get caught up in the moment or they just want to say what you want to hear because they don’t want to make things uncomfortable.

All that said, I feel like this is a pretty specific thing for him to say. If he said “after the weekend,” I’d give it until Tuesday. If you don’t hear from him by then you have three options:

1. text and ask him how the weekend was to spark a conversation

2. text and ask him what night works for him to go out this week

3. don’t text and wait to see if he texts

My suggestion is option 2. I never recommend waiting around to the point of being uncomfortable. If he said “after the weekend,” and you’re now at Wednesday or Thursday or Friday and still haven’t heard, that’s not comfortable! And it’s easy to start spiraling when you’re not sure if you’ll hear from someone.

That’s why I always suggest just sending the text—but it’s with a big caveat that the text should always have a purpose, and that purpose shouldn’t be to get them to text you back (like in option 1).

Option 2 is the most powerful option because you’re not beating around the bush. He’ll either reply and tell you when he’s free, or he’ll reply with something wishy washy, or he won’t reply at all.

If he does either of the latter two things, I’d write this one off and move on. You deserve someone who is consistent and who does the things they say they’ll do!

👀 Texts to send after a date if you want to go out again

Want to be suggest a topic or submit a question (anonymously) for a future send? Send me an email here.

This week on the pod:

Stop Waiting For Potential

this week we introduced our new podcast segments:

• "what should I say?" where a listener asks what to say to their partner, friend, family member, coworker, etc. in a certain situation.

• "keep going or call it?" where a listener describes their scenario and ask whether they should stay in a relationship/go on another date/continue a friendship/etc.

• "expanders" for dating/relationship success stories to help be each other's expanders

• "a letter to my younger self" where a listener writes the advice they'd tell their younger self about dating/life

• "friendship files" specific to friendship dilemmas/conflicts

• "not proud of it" anonymous confessionals of the things we do that we wish we didn't

click here to listen — or reply to this email if you want to write in for any of these topics!

*Anyone who leaves a rating and review on the podcast this week gets a special $5 treat from me. Just reply to this email with a screenshot of your review!