The OGs In African American Female Group Travel Experiences
Encouraging black women since 2006

The marriage proposal
The 2nd one since arrivng in Italy


I has been a bit quiet lately, while focusing on the possibilities with a man I met 3.5 months ago on Tinder prior to arriving in Milan.


He is IT Specialist that is raising 2 children alone after the death of his wife 11 years ago. The children are a boy 17 and girl 21 years of age. I normally do not date men with children but decided to explore this one because the children are older, and he is so dang nice. Soon after my move to Milan, he asked me to be his girlfriend and I agreed.

Our time together has been nice with the except of his availability due to his children, mountain climbing every Saturday and living 45 outside of Milan. He still cooks dinner every night for his kid (17 and 21) and drives them EVERYWHERE they need to go, like they are 9 or 10 years old. He is like an Italian mother, not wanting his children to be independent.

I understand his need to protect them more due the loss of their mother but this is a man that goes mountain climbing EVER Saturday. One bad move could cause him a major injury or lost of his life. To me, this is more of a reason why his children should know how to take care of themselves at their ages. I think deep down he likes the dependency.


During a talk a few weeks back, he said there would be an expectancy of me to stop working if we every married. I laughed it off with a comment about my shoe budget.

Our time together is basically one date during the week, in which he cannot spend the night due having to drive the 17 year to school every morning. His son could ride a bicycle or Vespa to school, it is less than 2 miles from his home. The 21 year has random thing needs, like him driving her to dance classes 3 days a week. If we have a date on Friday night, he can not stay over because of his weekly climb starting at 6 am. He normally arrives at my house on Saturday evening about 8 pm. He does take the time to plan thoughtful dates but he always has to leave early on Sunday to have lunch with his son.

Yes, we have talked about me meeting his kids (I used the term kids lightly). I have insisted that is a causal meeting outside of him home, so they do not feel that my plan is to Invade their space. It has not happen because the 21 year old seems to always have somewhere he need to drop her on Saturday evenings before he comes to my place. I have made it known that I am unhappy about the amount of free time he has available and he responded by taking a Friday off from work to spend with me. It was a nice jester but not a solution. I decided to try to be a bit more flexible because he was trying to accommodate me, but the reality is, he just does not have the time and this not the type of relationship I want. It feels like I am dating a married man or in a long distance relationship. Neither scenario works for me, but he so dang nice that I have been just going with the flow, UNTIL...

Weekend before last, we are having dinner at a really nice restaurant. We are joking around as normal and he asked if he could call me his fidanzata, which means fiancé. Thinking he was still joking, pretended to not know the meaning of the word and asked for clarity. He said very seriously, it means the women I will marry. I laughed loudly and said you cannot call me that without a ring. He reached into his pocket and pull out a little box.


For a moment my heart stopped while I was thinking NOOOOOOO as I went into flight mode looking the exit. When the blood returned to my brain, I realized he was planking me and played along with the joke by asking when will we get married, because I a pretty busy these days. He said, maybe 6 months. I said, 9 would be better. I said, okay with a knowing laugh as we play chicken to see who will break first. He asked, why I have not opened the box. I said, because that was the man's job. He gave me a smile as he opened it.


The blood left my brain again. FU@K HE IS NOT JOKING! WAIT Yes, he is! That is not real because Italians do not give engagement rings, only wedding bands. He almost got me good! I said, cute but it is a bit small. I am a tall women and need something bigger. He did not reply but I could tell something was wrong. Normally, my arrogant remarks make him laugh. This time NOTHING!

WAIT, is this real? He replied, yes. Again the blood leave my head. This time I am ready to run! I excuse myself and go (almost running) to the bathroom. I go into a stall and sit. Think Fleace, think! I keep repeating to myself. How did I not see this coming? My last proposal, I saw that it was it coming and broke off the relationship before he asked to save my ex the embarrassment. This one blindsided me. It has only been three dang months. What do I say? Sh@t, why isn't there a window in this bathroom?

I pull myself together and go back to the table hardly able to make eye contact and say WOW, I do not know what to say. We sat quietly, just looking at each other. I knew, I had to speak first.

I took a deep breath and said I was not expecting what happen and not ready for such a big decision. I asked him, how do this is right for him. He said he knew on our first date. I smiled because I was such a bit@h on our first date. Playful but still in I don't give a damn if you like me or not mode. As a matter of fact, most of our dates have a little pinch of that from me. Like, mountain climbing, he like the challenge. I pick up the box and tell him of course I was joking about the size. He laughed and told me I was not joking. We both laughed.


I handed him the the box and said hold this until it is the right time for us both. He said, of course. We finished the evening drinking and being extra flirty and the next morning her was gone to have lunch with his son.

We went back to dating as normal but with a more serious feel at least in my head. I found myself thinking is this really what I want. Is he the one or am I just settling because he is nice to me?

As luck would have it. My ex from Florence came to visit me last weekend as we had planned prior to me moving. Since my ex would be staying at my place, I invited my current boyfriend to meet him. At first he was reluctant but later agreed to us all having drinks together.


My ex invited a woman he met while on vacation that lived in Milan. The afternoon went well and later at my home my ex and I had conversation about each other's dates. I mentioned that I liked the chemistry between him and his date and suggest that reconsider his decision not to see her again due to them living in different cities. He wanted someone that lived near him, so they could see each other often. He had no plans to move to Milan and moving to Florence would be a bad career move for her.


To him it would be a dead-end relationship. The more we talked about my currently relationship, the more I thought about maybe I too was in a dead-end relationship. I am with someone that wants to marry me, but marrying him would change my life dramatically, starting with a move to another small town. I learned from my time in Florence,  that it would be difficult for me to live in small town in Italy. I would not be happy, not even if in love. My husband would be happy, but I would be miserable.

I do not make those type of sacrifices any more! I made a promise to myself to put my happiness first. Most of you that have been following me for a while know that my motto is; “we both can be happy together but, if someone has to be unhappy in the relationship, it will not be me!”

After taking some time to think, tonight I broke up with my Milan boyfriend. Almost a year to the date that I broke up with my ex-boyfriend in Florence. During the break-up conversation, told him all the wonderful things I liked about him. There are many! We agreed to continue to date but not in committed relationship. I want to date other people without feeling that I was cheating on him.


He thanked me for being direct and honest. Italians are not known for directness. Maybe when his children are older and on their own we can try dating seriously again. Unfortunately, in Italy, that may not be until both children are in their 30s.

Until then... I will continue to be a HAPPY Black Girl in Italy.

P.S. For all of you that think there no good guys on dating apps, know that they are out there. In 12 months, I have broke up with two of them. I had amazing time with both of them, but did the right thing and released them to meet the real love of their lives




Your Italy Specialist


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