Life Advice



Erika Ettin: Clients seek answers to dating dilemmas

Erika Ettin, Tribune News Service on

Published in Dating Advice

Every so often, I get a truly great dating question or two from a client that I want to share with my readers. This week, I’ll be sharing two of these, one from a man and a woman, respectively, along with my responses:

Q: I went out with a woman a month ago for coffee (outdoors!). Then I went out of town, so we just got together again this past week. I ended the date with a hug since I didn't want to rush things. I'm going to see if she wants to get together again this weekend. She's really nice, and I think this could grow into something, but I didn't want to rush into anything.

At the same time, I'm trying to set up two dates with other people who I'm curious to meet. Sometimes I think it's just bad timing so I don't want to give up on these prospects.

Do you have any advice or a mindset I should have for these situations? I don't want to lead anyone on. At the same time, if I keep hugging her at the end of dates, this will kill any chance of progressing either. Like a self-fulfilling prophecy, my indecisiveness may kill the chance of progressing either? My friends think I should always go for a kiss at the end of the second date. Is there a rule for this?

— Gene, 33, Boston

A: Thanks for sharing what's been going on. To answer your question, you're not leading anyone on at all by scheduling these new dates. That's the whole point of dating — to get to know someone to see if you'd like to pursue more. Not bad timing at all! Just dating. Also, you're allowed to kiss one woman (maybe make sure she’s vaxxed first?) and still go out with others until you decide if/when you'd like to see someone exclusively. It sounds like you're putting a lot of pressure on yourself to decide something, but there's nothing to decide right now at all.


I agree if you don't make a move by the end of a third date, it will generally shift you into the "friend zone." There's no rule, but in general, I would go in for a kiss when you're feeling it, be it a first or second date. It shouldn't be prescribed, though, like always at the end. If you're feeling a moment in the middle, go for it. If you're not, don't. But, if you never make a move, a woman will assume you're not that into her or are too timid, neither of which is a positive assumption. In general, if she's agreeing to see you and is enjoying herself on the date, she'll likely be open for the kiss, but she's waiting for you to make the move. You could always say, “I’d really like to kiss you right now,” which is essentially asking for her consent. Or even, “May I kiss you?” Then it won’t feel like you’re going in so blind.

Q: "Good-looking" is so subjective, and I can overlook certain good looks to find a good quality man, but I can’t just fake it if there's no attraction at all. If the chemistry isn’t there, it makes things extremely awkward for me. I end up walking away from the date feeling like I’ve wasted their time or, even worse, I got their hopes up. And of course personality plays a huge role, but I haven’t dated a man I wasn’t attracted to because he was extremely intelligent or had it all together financially. How do I reconcile this in my head?

— Eileen, 48

A: At a certain point, it's important to explore and see what's out there, just as you'd want someone to do for you. No one is asking you to fake anything, but when you meet someone and get to know him, you may see something. Or not. And judgments shouldn't be made in the first five minutes, if you can help it. With people who we're extremely attracted to at the offset, we tend to overlook really important things in a relationship. There is a happy medium between someone who knocks your socks off looks-wise online but isn't a good fit and someone unattractive.

Do I want you to fake it? Of course not. But, in the end, a date is a date (even a bad one), and no one has wasted anyone's time. It's just about seeing if there's a connection. Never feel guilty for that.

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