Last month, we asked you to submit your burning inquiries. Now, the answers are in. Read on to see if your question was selected and maybe learn something along the way—because who doesn’t need a little (un)solicited advice?
Get to Know the Expert
Meet Jenn

Hello, internet. I’m 35 years old, in a relationship, but had previously been single and (what felt like) professionally dating for the past three years. Prior to my long stretch of singledom, I had two long-term (and more than a couple short-term) relationships under my belt. I know the dating app scene a little too well but also prioritized meeting people out in “the real world” (aka, I know dating). I’ve been in love a couple of times, had my heart broken many times, and still—somehow—always come back for more. I’m undecided if that’s optimism or masochism, but either way, I feel well equipped with my decades of dating and relationships knowledge to help you through the hard-hitting questions.
There’s a guy I like a lot, but he has a girlfriend—what do I do?
Who among us hasn’t fallen for someone who wasn’t available? I certainly feel your pain; however, chasing unavailable people rarely yields good results. There’s no scenario where someone doesn’t get hurt, and, unfortunately, it will likely be you. Carry on with your life, date, meet new, interesting people, and if that person ever becomes single on their own terms—you can, in a healthy way, pursue them.
I currently like a person who is probably a player, should I get out of there?

When someone shows you who they are, believe them. I know that’s a major cliche at this point, but my experience has shown me that’s 100% true. If you’re getting player vibes, it’s because they are likely a player. And if you’re looking for a serious relationship, this person may not be the headspace to give you what you want.
What should I wear on my first date?
Okay, first, send me a voice note after the date and let me know how it goes, okay? Second, determine whatever your personal style version is of, what I call, the “first-date uniform”. This is an outfit that you can grab for every first date that makes you feel cool and confident. For me, that’s my go-to jeans, fitted black cardigan, and heeled black boots. Make it your own with accessories, hair, and makeup. The real key is picking something you know makes you feel good—bringing confidence to a first date changes everything.
Would it be wrong to reach out to an ex-friend that I cut ties with over a year ago?

It’s not a hard no, but take a minute to think about why you decided to cut this person out of your life. Is there evidence they have changed? Will you be able to set boundaries this time around? Friendship breaks ups are so hard and no one talks about how to navigate them, but they’re like romantic relationships—they require work, but should be healthy, happy, and supportive for the most part. If you don’t think this person is capable of that, keep the door closed.
Is long distance worth it?
Bear with me, this is nuanced (I’ve done long distance twice, so this is an area I have a lot of opinions on). I think distance can be worth it, but you have to have a plan. If you’re dating cross-country (or even just cross-state) with no plan for if someone is moving, when that person is moving, and what that person will do when they get there—then you may be looking at trouble. But, if there is a reasonable timeline for you both to be in the same place and it makes sense for both of you personally and professionally to make that leap, go for it! Long distance can absolutely be worth it…as long as it’s temporary.
How do I set expectations in a relationship?

All together now: communication. If you want something, you have to say it. For things as small as wanting “good morning” texts to as big as “I want kids by X year”, your partner will never know unless you tell them. And if they don’t align with your expectations, then they may not be the right partner for you. Remember, you’ll only be considered needy by those who don’t meet your standards.
Any tips on staying single? I’ve been in a relationship my whole life.
Welcome to a very exclusive, very chic, very cool group of people—those who embrace being single. As soon as you start mentally framing your singlehood as a positive thing, the sooner it’ll be a place you’ll want to stay. Think about it: Your primary focus is you. Come and go as you please, talk to whoever you want, plan trips whenever works for you, flirt, spend endless amounts of time with your friends, be a little selfish, you’re on your time, baby!
What do you think about online dating?
Well, I’m in a relationship because of it, so I’m definitely pro online dating. With that being said, I slogged through the muck and the mud (I went on 27 first dates in 2024 before meeting my significant other), and if you’re not in a place to play the numbers game, put in the time, know some of it will be wasted, and learn to laugh it off, then I would put a pause on that download button. But, if you’re down to meet some people, collect a few good stories along the way, send some silly voice notes to the group chat, and put in the time—go for it, I truly believe your hard work will pay off if you’re in the right mindset.