Love Letters

Two friends, one dating pool

Q. I have a question about dating etiquette. I’m a divorced, 50-year-old woman. Life is good — I have great kids, a job I love, friends (both male and female), a cool living situation, hobbies, etc. I’m healthy and attractive. But because I have no primary companion, I’m Internet dating.

The complication? One of my female friends is in the same situation. As a result, we share the same target demographic. It shares us. It’s like !@#$% high school.

A few months ago, a few of us were out to dinner and she said she was dating a new guy. I got a weird feeling in my gut. I asked for a photo. Sure enough, I recognized him immediately and told her so. I had never dated him — thankfully — but he’d been a consistent visitor to my profile and had asked me out a number of times. I had little interest in him, so it was nothing more than a footnote, especially since it didn’t last with them. Whew.


It almost happened again last weekend. I was surfing the dating site and came upon a profile of a man who seemed like he’d be an interesting date. I looked at his profile a few times and thought about writing to him but I didn’t. Frankly, I didn’t know I was on a timer. As it turns out, she asked him out first. In fact, she blew off dinner with a group of us in order to go out with him. When she showed up very late after the date to tell us all about it, I recognized him from her description. I told her that I’d seen his profile and found him very attractive.

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According to her, their date was “amazing.” She saw potential for “something real.” She said all the things people say after a promising first date, hope against hope. At that moment, I knew I had to drop any idea of contacting this guy or ever dating him. I did.

The next day, however, he contacted me. He wrote to say that he was interested and asked if I had reciprocal interest. This, after the “amazing” date with my friend.

What to do?

A mutual friend, a woman who knows us both and who happened to be with me when the e-mail came in, said that dating him would be worse than sleeping with a woman’s husband. That seems pretty dramatic to me, given that they’ve only been on one date, but what is the protocol? It’s been about a hundred years since I’ve been in this kind of situation. Have we evolved since high school? What does it look like?


Would it be helpful for me to say, “Um, Amazing Date is still in aggressive search mode” — or would that be too much like gloating? I care about her and don’t want her hurt. But if this is a “what’s the big deal” situation, it’d be nice to know that, too.

There are plenty of fish in the sea. I know all the clichés. But, really, what’s the right thing to do?


A. Going on the date would not be worse than sleeping with a woman’s husband (that mutual friend of yours must like to exaggerate). That said, I don’t think that you should pursue this man. Your gut is telling you to stay out of the way.

There are no real rules here, but I recommend telling your friend that you need to know what to do when she mentions a man who has contacted you both. Tell her that there needs to be more frequent disclosure — especially after a second date — so that you stay out of each other’s way. If she asks about Amazing Date, go ahead and explain what happened. If not, keep it to yourself. Also, be more proactive about telling her who you like. She can’t have dibs on everyone.


Maybe after a second or third outing, she and Amazing Date will fall madly in love and then you’ll have the Internet to yourself. But for now, you need to check in — fairly frequently — about what you’re doing. There are plenty of fish in the sea, but it’s a small sea. You’re bound to keep bumping into each other.



If the guy contacted you, and you are interested in meeting him, then do it. Don’t make it complicated by bringing the friend into the decision; she dated the guy once. What if she hadn’t told you about it?


Sorry, but if you do care about this friend of yours, you can’t go on a date with this dude. And why would you want to? I think its fine if he’s still keeping his options open, but there is no need to tell your friend that you got a message from him. Just say something like, “Did you ask if he is seeing anyone else?”


If your friend and you are going to compete over Amazing, he is going to be the only winner.


You’re 50 — act it. Perhaps I’m injecting tone into your letter that isn’t really there but you seem to be the one who needs to grow up. Speak to your friend directly instead of through third parties — and stop passing notes.


Here’s the thing with online dating . . . they’re not waiting around for you. If ya snooze, sweetheart, ya gonna lose.


By all means have a talk with your friend and come to an agreement about sharing the same dating pool and honor it. If you both determine that it’s “each woman for herself,” then fine.


Have you tried not using the same dating website?


Seriously, while the letter writer is dipping her toe in the online dating pool, her friend is diving in and doing the backstroke. She needs to pick up the pace or all the swim buddies are going to be taken.


One time, I got an e-mail from what appeared to be a very nice gentleman. A friend got the same exact e-mail, word for word. I let the guy know that somehow my friend got an identical copy of what he sent me, that Boston was a city, but not a big one, and wished him the best of luck. It’s that easy.


I have no idea what you should do but I really enjoyed reading about it.


Column and comments are edited and reprinted from Meredith Goldstein can be reached at mgoldstein@