Valentine’s Day Dilemma

Good Morning Guys,

A guy on match dot com emailed me about three weeks ago and we hit it off immediately. (He’s one of three I actually gave the time of day to.) Two days after the first email, he gave me his cell number because he didn’t want to seem impolite by asking for mine. I sent him one text first. (I’m a little old fashioned in he sense that I believe the guy should be the one to initiate contact in the beginning, but he did put the ball in my court by giving me his number.) The very next day, after several texts back and forth, he asked me to dinner the following evening. We met in a public place, and I made sure two friends knew the time and place, just to be on the safe side. He asked to say the blessing, and at that point I was sold. Throughout the conversation at dinner, I discovered this too was his first time actually meeting someone off the internet…and we both had only given our numbers to each other, no other. After dinner we went our separate ways home.

The next evening, he asked me to dinner again for Saturday. Date Two was even better than Date One. He opens every door, prays over each meal, and treats me like a princess. Downside is, he told me he was leaving Wednesday for a three-week business trip.

By Monday, I was dreading the three-week trip and sent him a text in response to one he sent that simply said, “I miss you and was just thinking it would be nice to see you before you leave Wednesday.” He responded immediately and said he was thinking the same, and he asked me to dinner. We went to dinner, then back to his place for a few games of pool. My co-worker told me before Date Three that you know after Date Three if you’re into someone or not, and there’s no doubt in my mind. He texts me every day. I know he’s as interested in me as I am him, That’s not my dilemma. My dilemma is Valentine’s Day falls during his three-week business trip and only 3 1/2 weeks after out first date. We haven’t discussed Valentine’s Day, and I’m not sure if I should or shouldn’t bring it up. I’ve never been big into Valentine’s Day, but I’ve also never had a guy treat me with the respect and chivalry that this guy has. I would love to see him BEFORE he returns, but I can’t just invite myself to visit across the country.

So I’m wondering what your advice is as to mentioning Valentine’s Day?

Newly Dating Valentine


Dear Newly Dating Valentine,

Thanks for your question.

Since you’re an old-fashioned girl, as you say, then stick to that mantra and let him bring it up. It’s likely, if he’s as into you as you are into him, that he’s also thinking about it, and wondering what he should do or not do.

But let’s start from the beginning and address Valentine’s Day from The Guy’s Perspective.

Valentine’s Day can put a lot of pressure on a guy. (Not to say, it doesn’t for women as well.) Even if our partner/girlfriend/wife says it’s not a big deal, we’re not that stupid to actually believe that we can blow it off. We know from experience that when a woman says, “You don’t have to get me anything,” that this is really a way to see what we might do. At some point we can recall the year we took these words at face value, and the fallout was precipitous. We’re not looking for a repeat performance. So now, we do our best to make Valentine’s Day special.

At the very least, a guy might get some flowers or chocolates, especially if he’s been with his partner a long time. In a “newer” relationship, a guy might keep trying to up the ante, hoping to impress his prospective long-term partner. But when it comes down to the very first Valentine’s Day, especially in a newly blossoming relationship, a guy will question himself over and over.

Is this too much? (I might scare her away.)

Is this not enough? (I don’t want her to think I’m cheap.)

Should I stick with the tried and true? (I don’t want her to think I’m boring, or lack creativity.)

Should I get creative? (I might completely miss and then she’ll either think I’m weird or creepy?)

Maybe I should do nothing? (She’ll think it’s too soon. I don’t want to scare her. See above.)

In your case, he’s thinking of all of the above, and it’s likely he’ll settle on some combination, even possibly just an acknowledgement of the holiday. There’s not much you can do here. Let him take the lead on this.

Last point: Don’t freak out if he doesn’t bring it up. It’s most likely because he’s uncertain and feels awkward.

Your relationship sounds like it’s off to a great start. Enjoy!


ps. Please spread the word about us on social media. @TGPBuzz. Thanks!

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