(Forgive me — this is a totally heteronormative post because I’m a woman who dates only men. I imagine one could take all my rules and apply it to any dating permutation…)

At 48, and after two marriages, I’m dating again. But thanks to our wonderful Facebook community, I never feel alone in this endeavor. I’m actually finding it easier now (and more entertaining) than I did ten years ago; these days it seems like truly everyone and his mother is on OK Cupid or Bumble, so there’s zero social stigma and tons of choice. It’s almost fun! My partnered girlfriends are loving it too — they swipe for me over dinner all the time — both for kicks and because they think I have questionable taste LOL.

Thousands of Woolfers are out there on the apps, and we’re sharing our tips and stories every day, so we thought we’d compile a list of what we consider basic rules & guidelines for those starting out or getting discouraged:

1. Unless you’re quite confident you’re going to like the dude, don’t agree to drinks or dinner. Drinking will make you more likely to like (or kiss, or even sleep with) someone you might not actually like sober, and dinner can just be way too long. Start with a walk in the park, or coffee, something nice and sober.

2. Don’t waste time with too much emailing or phone calls beforehand. Just meet.
You can actually fall in love with someone over the phone and then when you meet them in person feel ZERO chemistry. This has happened to me and it’s very hard to extricate yourself, trust me.

3. If you wink at or write to or swipe someone and they ignore you, DO NOT take it personally. You have no idea what’s going on in that person’s life. He may be involved with two other people; he may have a particular hang up about your hair color; he may be out of the country or in the hospital; he may only like women who show pictures of themselves in bikinis. You simply won’t know, and this guy doesn’t know you from Eve, so it’s not personal. He’s just not the one.

4. You may be more generous person than I am, but I say don’t respond to all the completely uninteresting people who message you. It’s a huge time suck, and you wind up arguing with strangers about why you don’t want to go out with them. I feel like the better tactic is to ignore. For follow-ups on dates that you don’t want to pursue, come up with a standard one-or-two liner that fits all occasions, something like “Dear so-and-so, you are a great guy, but I don’t feel we were a match. Good luck to you.”

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5. Be proactive — set some time aside every week to look around and click on or write to men who appeal to you. Even if they don’t respond, it’s a helpful exercise in thinking about what you like and don’t like, where you might be willing to be flexible, etc.

6. Keep your profile up even when you are discouraged. You can take breaks from how intensely you engage with the sites, but keep your profile up. It’s a numbers game, and an evergreen one. There’s always another guy out there hitting the market (getting divorced, widowed, ready to date) and you just never know when a really intriguing person is going to send you a sweet note… and he will, I promise.

7. Make sure you employ the old saw “show, don’t tell” when writing your profile. If you’re funny, be funny; if you’re serious and very focused on finding someone with a lot of intellectual heft, demonstrate your own. Your friends should be able to read your profile and know it’s you, so include a few tidbits that are particular to you, which also gives potential suitors something to ask about or hook into when they write to you.

8. Pictures matter, and they should be current. I’ve heard so many men complain about showing up on dates to meet women who look nothing like their pictures, and really, who does that serve? Make sure the photos are flattering, but accurately represent you, and change them up every now and then if you aren’t getting the kind of responses that you want.

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9. If you’re striking out right and left — not getting any dates, feeling like you can’t get interested in anyone — have a trusted friend (maybe a man) read your profile. If you get the thumbs up there, you might consider looking at a) whether you really truly want a relationship and/or b) whether you’re being too picky/pessimistic/cautious. Something in your energy is foiling you, and you need to look inward to figure it out. Might be a good time for a therapist. Because I promise you, there is someone out there for you — likely many people — and if you’re not finding them it’s not because you aren’t appealing or pretty or smart enough. It’s something internal and deeper.

10. I hope I don’t have to tell you to use a condom, but use a condom. And HAVE FUN!

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Nina Lorez Collins
Nina Lorez Collins a lifelong New Yorker, born there in 1969. She graduated from Barnard College in 1990 and got a Masters in Narrative Medicine from Columbia in 2013. She has four kids who are mostly launched, is the founder and author of WWVWD, and serves as a trustee on the board of the Brooklyn Public Library.

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