Dating Experts Weigh in on Your Love & Relationship Questions

Last month, we asked you to submit your burning love and relationship questions. Now, the answers are in. Meet our two pros with two POVs—sometimes they align, and other times have completely different stances on your quandaries. 

Read on to see if your question was selected and maybe even learn something along the way—because who doesn’t need a little (un)solicited advice?

Get to know Expert #1

Meet Jenn

I’m 34 years old, single, actively dating, and have two long-term (and more than a couple short-term) relationships under my belt. I’ve spent more time than I would like to admit on the dating apps, but also prioritize meeting people out in “the real world”. I’ve been in love a couple of times, had my heart broken many times, and still always come back for more. I don’t know if that’s masochism or optimism, but either way, I feel well equipped with my decades of dating and relationship knowledge to help you through the hard-hitting questions. 

Get to know Expert #2

Meet Cristina

I’m 45 years old, have been with my partner for almost twenty years, and we have a daughter in kindergarten. I did my fair share of dating (in the dark ages before dating apps) and had a string of love connections and epic fails before meeting my partner in a bar. Since then, I’ve played romantic advisor to many friends as they navigate the puzzle that is dating in their 20s, 30s, 40s, and 50s. I’ve heard it all and am ready for more.

Q: How do I know if they like me back?

Jenn: I’ll let you in on a secret—if someone likes you, you’ll know. When you like someone, you find excuses to talk to them, send them funny memes, take an interest in their life, ask questions, etc. They’ll do the same for you. Sometimes, when the subject of our adoration isn’t giving us the above, we look for clues in the minutiae, hoping to find something to validate our feelings. But trust me, the answers are right in front of you.  

Cristina: I like to say that we should all be trusting our gut to guide our heart. Your instincts matter, and usually if they are expressing interest in who you are, they’re interested—period. For my 5-year-old daughter, sussing out who she connects with is quick and innate—it’s amazing to watch, actually. Kids are just so open. Those senses dull as we get older but believe that it’s still in you to know.

Q: Do you believe in right person, wrong time? 

Jenn: No question, 100% resounding yes—timing is everything. You can meet a person who is great for you, perfect even, but if the circumstances for both of your lives don’t align, it won’t work. I also believe there are multiple people for us. So, just because the timing didn’t work with one, you can still find that unlock with someone else. 

Cristina: It’s hard to be sure if a person was right if the timing was all wrong because it’s a huge determinant of compatibility. I can’t say that I would have connected with my partner in the same way had I met them a few years later than I did. It may be woo-woo, but I do believe, and this goes for non-romantic relationships too, that the right people will come into your life when you need them the most (and sometimes even re-enter your life). One of my dearest friends, after a truly hellacious divorce, reconnected with someone she had gone on a few dates with twenty years ago and got married: they fell in love for the first time, the second time around. 

Q: How do I spark a conversation with my crush?

Jenn: There are two ways to approach this based on your relationship with the person.

#1: I know this person well.

In that case, look for something you two have in common. Example: A band you both love dropped a new album—ask what they thought of it. Or, a video you saw (funny is best) reminds you of them—send it their way. Think of it as opening a door to communication and growing it over time since you two have a foundation. 

#2: I don’t know this person well.

When in doubt, compliment it out. But, try and ask a question to keep a conversation going and build a base. Instead of “I love your jacket,” try, “I love your jacket, is it vintage?” Rather than “Cool band tee, I love them” try, “Cool band tee, have you ever seen them live?” This allows the conversation to go somewhere. 

Cristina: Finding common ground is huge. At least as a jumping off point. You don’t need to like all the same stuff, but discovering something you share is an ideal way to open a door. I see it working for my kid all the time: “Do you like ninjas?” “Yeah, me too!” or “Oh, you don’t like ninjas? I love riding my bike, do you ride? Let’s do it together.” (Actual playground conversations.)

Q: How do I move on?

Jenn: If I had a foolproof answer for this, I would be a wealthy woman. But, as someone who has had many breakups, I can say what works for me is staying busy. That doesn’t mean not feeling your feelings—do that. What it means is not giving into wallowing. Lean into your hobbies, and eventually, you won’t have to be so purposeful about occupying your time because your life will be back to normal. 

Cristina: Moving on from a relationship or even a friendship that is no longer working is a process, and it’s incredibly hard not to spend a lot of time and energy mulling over everything that went wrong. As someone who has had to move on from multiple romantic, familial, and friend relationships, here’s my MO: I try (and, yes, don’t always succeed) to not look back in anger, to preserve what was good in my head, to learn something—anything—from what went awry, and to always, always distract myself along the way.

Q: How do I give more to my partner than just gifts? 

Jenn: Listening, truly listening, is the best gift you can give your partner. This will help you give in a way that’s beyond the superficial and it’ll make you a better significant other. And it’s free! 

Cristina: Being present with someone in our collective age of distraction and ever-shortening attention spans is truly the greatest gift. Nothing makes my partner happier than me ignoring my phone when we’re out together doing anything.