I’ve started dating my high school sweetheart again, but it seems he hasn’t grown up much

Dear Wayne and Wanda,

I’ve recently started dating my old high school sweetheart again. Now he’s 33 and I’m 31 and it’s been 12 years since we broke up.

I am having a hard time understanding my feelings. I definitely love him, but I feel like I’m having a hard time falling in love with him again because of his immaturity. I worry he hasn’t matured much since we last dated. That was a reason we originally broke up: I was ready to start a career and think about the future. At the time, he was very happy-go-lucky, which can be a good thing. But he also didn’t have many future goals and he didn’t seem very serious about our relationship going to the next level.

Today, I’m a mature adult with my own house and I support myself. He still lives at his parents’ house, and I admit, this really bothers me. Please help me look past this or tell me the honest truth if you think he’s never going to grow up. Thank you!

Wanda says:

Many years ago, I reconnected with a high school ex-boyfriend. It was quite the ego boost when he reached out immediately after his divorce (in hindsight, a major red flag that I mistook for a romantic gesture). We went out a few times, had some drinks and laughs, and I recalled the thrill of youthful romance. Alas, while I noted his charm and warmth that had initially attracted me to him all those years ago, I also remembered all the reasons we broke up — like his complete lack of ambition or goals.

It can be easy and convenient to rekindle and recycle past romances. Sometimes it works out and delivers a happy ending. But a good friend once said that, after a second bad breakup with the same person, usually the reasons we broke up in the first place still remain valid when we attempt to couple up a second or third time.


You didn’t go into great detail about your boyfriend, but I definitely wouldn’t say the fact he lives at home is necessarily a deal-breaker. It’s more and more common in today’s costly housing market to see people taking advantage of multigenerational living arrangements as a way to make ends meet, save money or help out family members in need. The question is: Is this his forever plan, or a temporary arrangement? Depending on his choice and situation, neither choice is wrong or deserves judgment. But it may be that his choices and lifestyle aren’t compatible with your own present and future plans.

Wayne says:

Still charming, but still living with his parents. Still flying sparks, yet still lying around. So you’re saying not much has changed since high school? Then why expect anything different moving forward?

You still have deep feelings for him — that’s understandable and may never change. It’s the bittersweet symphony of long-lost loves. But some relationships are best left as special memories and important life lessons. I think he’s already shown you why that’s the case here.

Fact is, he may never evolve into your vision or expectation of a mature adult, professional equal and compatible partner. And you shouldn’t invest your time and energy trying to get him there, especially if it’s something he doesn’t want to grow into. You’re likely to spend this relationship feeling frustrated, disappointed, and wondering why you rekindled this fun-at-times fire.

Trust your gut, trust your heart and trust your history — snuff out this old flame and move on to bigger and brighter things.

[My ex dumped me before the holidays last year, and now he wants to get back together]

[Snowmageddon dampened my girlfriend’s outlook on Alaska. How can I turn things around?]

Wayne and Wanda

Wanda is a wise person who has loved, lost and been to therapy. Wayne is a wise guy who has no use for therapy. Send them your questions and thoughts at