This week, we have three very relatable dating questions:

Question: I really like Gerry and don’t feel like sifting through other profiles. But is that wise? Should I still go through the motions as backup options until my three-month Match subscription ends, in case Gerry and I fizzle? I know he likes me.

-- Jane, 62, Orlando, Florida

Answer: Of course you should not go through the motions if you like Gerry! Enjoy yourself with him. We don't plan for contingencies. Should things not work, we can cross that bridge later. (There will always be interesting people around who like you and who you may like.) I fully believe that having a backup plan actually impacts the quality of the current relationship, and not for the better, so enjoy it and put the profile away!

Question: I’m in a dilemma. I don’t know what a guy I’m talking to wants. Around four weeks ago, we went on a date—happy hour and shared a small plate. I thought after the drinks it would be done, but he mentioned us walking to a networking event after. I was surprised but went along with it. We had a drink but didn’t like the crowd so left. He then asked if we should see a movie. I went along with it, and at the end of the date, he walked me to my car, which was very nice of him. We hugged and nothing else. We didn’t exchange numbers or anything.

I sent him a message the next day saying that I enjoyed my time. He texted back (through the app) 24 hours later asking for my number. He then sent me a text a day after I gave it to him. We didn’t text again after that. Then, almost a week later, he asks if I would like to grab a drink with him. Mind you, it’s at 7:36 p.m. and he wants to meet now. That’s not the kind of relationship I want, where I drop everything I’m doing to meet you when you please. I love spontaneously meeting up, but after a few dates. I decided to decline (even though I wanted to… and I was free) but said “maybe next time.”

A week later, I text asking him to grab a drink that week when he is free. He states he is going out of town for work Wednesday, and if he can get everything packed, he could meet Tuesday. Tuesday comes, and he can’t meet.

Yesterday afternoon, he sent a text asking if I would like to join him tonight for a networking event. I agreed and stated I would meet him there. He offered to pick me up.

I’m extremely confused. ... I don’t know if he is too busy, just wanting a friend, or just doesn’t get it. Can you give me your insight?

Thanks so much,

--Jackie, 33, Washington, D.C.

Answer: Plain and simple: He's not making time for you. (I think you know that in your heart of hearts.) He likes you ... enough. Inviting you to a networking event is not the same as going on a date. See how tonight goes, but then let him take the lead. If he wants to see you again, he'll make an effort, and if he doesn't, he won't. Trust me — you'll know when someone is excited to see you again.

Question: I have a question for you. I was invited to a speed-dating event this weekend. I declined to go. I have gone to this type of event and do not get matches. Do you have any suggestions? For a shy person, these events can be a little intimidating.

-- Susannah, 50, Pittsburgh

Answer: I certainly understand that, as a shy person, those events can be intimidating. The advice I'd give is to go with a friend (as somewhat of a crutch) so you don't feel like you're all alone there. That way, even a glance at each other can be reassuring.

For the short conversations, just remember that everyone is nervous. I remember that you're really into the arts and cultural events, so you can ask people if they've seen anything good that they'd recommend, which will hopefully start up an interesting conversation. And one of my favorite questions you can ask at a speed-dating event is, “If you weren’t here right now, what would you be up to?” You’ll really get some insight into someone’s lifestyle without it feeling too contrived.

Speed-dating is really just an opportunity to meet a lot of people in an efficient setting to see if you want to go on a "real" date with each other. So, as hard as it sounds, try to take some pressure off of yourself. It's just a few conversations with new people.

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