What would the Gentleman do?

[SaloSV]

Without divulging too much information about myself:  I am a 43 year old Catholic man who has been attending TLM for coming up on 5 years.  Lived a promiscuous life before returning to the church, but reverted with fervor after my father's passing.  Never married, no kids.

I've been looking for a suitable lady for some time, but the eligible bachelorettes at my parish are simply too young for me or are still considering religious life.

I went on a day trip to a monastery with my pastor last week, and he introduced me to a family who has attachment to the monastery.  We (myself, the priest, and they a family of 11) spent a relaxing couple of hours together over a light dinner and a fire.  We all then attended I Vespers of the Feast of the Immaculate Conception (which was a solemn ceremony, quite something) at the monastery. We again visited at the guest inn before my pastor and I left.  The family has 3 religious vocations at this time, one professed and two discerning.

It was a wonderful visit and a charming family.  I actually like the dad and everyone was very nice.

Two of the daughters were within my desired age range, eligible, and oblates of the monastery.  I found both of them quite attractive with high decorum, and pleasant to talk to.  I found myself more physically attracted to the older one, but made far more eye contact with the younger one.

I had planned to sending the family a Christmas card to express my well wishes.  Of course, I only have their mailing address... do I write the ladies, or do I ask the father for permission first?  The eligible ladies are both over 30.

Heck of a problem to have, eh? 

I welcome thoughts and opinions, but keep your chastisement to yourself.

Pax Domini

[Jeeter]

2 ladies! You sly dog, you!

Couldn’t resist. My thoughts are to send the Christmas card, and mention how you’d like to see the family again. When you visit again, you’ll be able to spend some time talking with the daughters to see if anything grows with either of them. If something does develop, it’s in a family supervised environment (why am I thinking the Sicilian courtship scene in The Godfather?), so the father and family will see it coming. No surprises, everything is above the table. As a 41 year old with 2 daughters, albeit a much larger age gap between them, I’d appreciate that.

[Credidi Propter]

If you send a card, I suggest sending it to the whole family and not even mentioning the girls. For the time being, just get to know the family better as a whole. If nothing else comes of it, everyone needs friends. In time, if something more exclusive is meant to happen between you and one of the girls, it will become more clear to you.

[SaloSV]

Good idea, and I think that's what Jeeter is suggesting as well.

But technically, there aren't two, there are four.  But only one of them actually knows they're a viable prospect with me.  Funny thing is, she is the only one of the four whom I have not met in person (met her online as well).  So even though I have been communicating with her for some months, things are not yet to a point where if I decide to move on to someone more suitable that she would be upset.  

I have a date Friday night with an old childhood friend who is in from out of town, and I will test those waters, but not expecting anything to come of it.  She went to a Catholic high school, but that's about the extent of her exposure.

[FisHook]

They sounds fine women. Spend some more time getting to know them. Pretty sure you will know soon who will be the one.

[SaloSV]

They sounds fine women. Spend some more time getting to know them. Pretty sure you will know soon who will be the one.

An update:

Suffice to say, the old childhood friend takes the cake.  And Deo gratias for that!  I won't bore anyone with the sappy details, but the first date turned into two, literally overnight.  Then I went to visit her in NYC last weekend and had the time of my life!

I can't imagine being with anyone else, it just wouldn't be the same.

Someone must have been praying for me because this is just too surreal to be happening under any other circumstance.  I have truly been blessed!

[SaloSV]

Well, I proposed on Feb 17th, she accepted.  Sorry, ladies, I'm off the market for good now!  Deo gratias!

There are signs all over, again and again, that this is the right move for both of us.

We are specifically requesting prayers asking for the intercession of:

Our Lady of Perpetual Help
St. Valentine of Rome
St. Augustine of Hippo

Thanks in advance.