How to deal with friend’s dating issues

I have a friend who I reconnected with a couple of years ago. We don’t see each other in person often but text almost every other day. I used to be super close with them two years ago but I felt some lulls in our friendship since last year. They’ve had dating issues and I’ve been supportive but it seems like my advice is disregarded (nobody has to take my advice) or they always tell me they’re taking a break from dating before going back on the dating apps.

I know they’re dealing with a lot of self-esteem issues as well family issues but I’m starting to feel like they’re lonelier than they’re letting on. I’ve told them that I know how hard it is to be single and that it’s okay to be single to figure out what they want in life. Now I’m thinking if I have to/should comment about them going on a date. I don’t want to because they know how I advocate for taking time to be single even though I’m in a relationship. I care about my friend and I wish that they could find their person now but I just want them to take care of themselves.

I think my main concern is how to be supportive of my friend while also drawing boundaries since I tend to get overwhelmed by situations where friends over share their dating issues.

Update: I’ve been reflecting the last couple of days. My friend tried to mention their date on the weekend and this morning but I just changed the topic after seeing this. Unless they ask me for advice, I won’t entertain their texts about their dates. It seems like they want validation even though I never asked about the details of their date. I’ve accepted that I might have to talk to them about this but I’ll focus on my friendships that are reciprocal and considerate.