Met him in Italy. Can’t stop thinking about him.

Send your questions about love, marriage, dating, single life, sex in Italy, missing some guy you met once – any relationship-related issues – to [email protected] or use this anonymous form.


Dear Meredith,

This past summer I took a trip to Italy and went on a few dates while I was there. One date in August went surprisingly well. I felt a connection with him from the second I saw him. 

We had a hard time keeping our hands off each other, and he was very distracted from cooking our dinner. Next thing I know, we’re in his bedroom. I had never had sex with someone. I have sexual experience, and have wanted to have sex with men before, but for physical reasons, that specific act didn’t happen.

So here I am, a 30-year-old virgin on a date with a sexy man in Italy. Lo and behold, there were no physical problems in this situation! It was the best first experience I think I could’ve had. I left that night and he messaged me the next day to make sure I got back to my vacation rental. The day after that, I was leaving and messaged him, “ I had a lot of fun with you the other night and just wanted to say that I’m glad I met you.” He eventually heart-reacted to my message, but that’s it. 

A few weeks later I messaged him, “Wish you were here in Roma!” because that’s where he is from. I didn’t hear back from him until a week ago. I had forced myself to believe I’d never hear from him again and it was just a one night stand. He messaged me, “I shouldn’t say this … but I can’t stop thinking about you.” (That message was part of a more graphic sext.)

While I was a little disappointed that the communication was so sexual in nature after more than a month, I couldn’t judge too harshly because I was guilty of the same thing – and thinking about him that way too. 

Reservations aside, I was still so excited to hear from him. We chatted a bit that day and he was begging me to come back and asking about the price of hotels in my area and talking about even meeting up somewhere else in the states. I was happy to hear his excitement. We started following each other on Instagram so we didn’t have to continue the conversation on Tinder. We chatted a little more on IG, sexted, and exchanged some PG photos. But since then, I haven’t heard much from him. I feel like I’m under a spell with how much I think about him.

Should I continue our casual relationship of flirting with the option to potentially see each other again someday? Or should I remove him from my life completely so I don’t get more attached?

– D&D


Is there a middle option here? Are you capable of dating, meeting others, and sending an occasional text to your Italian lover? 

Yes, I said lover. It felt right.

You could stop communication to make it easier to reboot your brain. But it would be nice to be able to keep in touch, know he’s out there, and maybe even revisit the situation later in life.

The best way to do that might be to say, “Hey, let’s meet up in a year.” Plan something tentative that’s super far out on the calendar. You’ll know it’s a big maybe, and there will be less pressure to make a date and arrangements. 

It’ll feel like you’re working toward the anniversary of an event instead of continuing a relationship that can’t go anywhere because of distance (and other reasons too, probably).

Remember, you’re feeling excitement, infatuation, wonder – but none of those things are love. Chemistry is great, but it’s just one thing. You had a super sexy night and you want another one. Understood! Have fantasies, but do not add narratives about him being a perfect partner, because that would be fiction – created by you. So far, he’s been great at one thing. That’s all you know.

Try to keep the messaging within reason, watch what you send (you don’t know this guy that well), and think fun thoughts. Even if you plan to see him in a year, you can have dates with new people, message others, and find chemistry elsewhere.

Sexiness and perfect nights can be found anywhere.

Even in, like, Medford. Or Quincy. It’s possible, I swear.

– Meredith

Readers? Would it help to stop communication? Is there a way to put this night – and connection – in perspective?

Love Letters

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